Aminopyrazinones

ABSTRACT

Aminopyrazinones and aminotriazinones of the formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is nitrogen or ═CR 4  --, R 1  is C 1  -C 4  -alkyl, R 2  is hydrogen, C 1  -C 3  -alkyl, C 1  -C 3  -halogenoalkyl, C 1  -C 3  -alkoxy, C 1  -C 3  -halogenoalkoxy, C 1  -C 3  -alkylthio, C 1  -C 3  -alkylsulfinyl, C 1  -C 2  -alkoxyethoxy, C 1  -C 3  -alkylsulfonyl, halogen or --NR 5  R 6 , R 3  is hydrogen or C 1  -C 3  -alkyl and Q is a group ##STR2## in which R 4  is hydrogen, C 1  -C 3  -alkyl, C 1  -C 3  -halogenoalkyl, C 1  -C 3  -alkoxy, cyclopropyl, C 1  -C 3  -halogenoalkoxy, C 1  -C 3  -alkylthio, C 2  -C 4  -alkoxyalkyl, C 3  -C 5  -dialkoxymethyl, halogen or --NR 5  R 6 , R 5  and R 6  independently of one another are hydrogen or C 1  -C 3  -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH═CH--, -- NR 9  --or --CR 10  ═N--, R 7  is hydrogen, halogen, C 1  -C 3  -alkyl C 1  -C 3  -alkoxy, nirtro or trifluoromethyl, R 8  is hydrogen, halogen, C 1  -C 3  alkyl, C 1  -C 3  -alkoxy, nitro --C.tbd.CH, or one of the groups   R 9  and R 10  independently of one another are hydrogen, C 1  -C 3  -alkyl or C 2  -C 4  -alkenyl, R 11  is hydrogen, C 1  -C 3  -alkyl, C 1  -C 3  -halogenoalkyl, C 3  -C 6  -cycloalkyl or C 2  -C 4  -alkoxyalkyl, R 12  is C 1  -C 6  -alkoxy, C 3  -C 6  -alkenyloxy, C 3  -C 6  -alkenyloxy, C 3  -C 6  -alkinyloxy, C 2  -C 6  -halogenoalkoxy, C 1  -C 4  -cyanoalkoxy, C 1  -C 6  -alkylthio, C 3  -C 6  -alkenylthio, C 3  -C 6  -alkinylthio, C 5  -C 6  -cycloalkoxy, C 2  -C 6  -alkoxyalkoxy or --NR 16  R 17 , R 13  is hydrogen, C 1  -C 3  -alkyl or C 3  -C 4  -alkenyl, R 14  is hydrogens C 1  -C 3  -alkyl, C 1  -C 3  -cyanoalkyl or C 1  -C 3  -alkoxy, R 15  is C 3  -C 6  -alkinyl,C 2  -C 6  -alkenyl, C 1  -C 6  -alkyl, C 1  -C.sub. 4 -halogenoalkyl, C 2  -C 4  -halogenoalkenyl or C 1  -C 4  -alkyl, substituted by cyano, methoxy, ethoxy, nitro, C 1  -C 4  -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C 3  -C 4  -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R 16  is hydrogen, C 1  -C 3  -alkyl or C 3  -C 4  -alkenyl, R 17  is hydrogen, C 1  -C 3  -alkyl, C 1  -C 3  -cyanoalkyl or C 1  -C 3  -alkoxy, R 18  is C 1  -C 3  -alkyl and C 1  -C 3  -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --SO 2  -- and m is the number zero or one.

This is a divisional of application Ser. No. 099,036 filed on Sept. 21,1987, now U.S. Pat. No. 4,295,486.

Aminopyrazinones and aminotriazinones

The present invention relates to novel herbicidally active and plantgrowth-regulating aminopyrazinones and aminotriazinones, processes fortheir preparation, the compositions containing them as active substancesand their use for combating weeds, in particular for selectivelycombating weeds in crops of useful plants, or for regulating andinhibiting plant growth. The invention furthermore also relates tointermediates prepared within the concept of the invention.

The aminopyrazinones and aminotriazinones according to the invention arethose of the formula I ##STR4## in which E is nitrogen or =CR⁴ -, R¹ isC₁ -C₄ -alkyl, R² is hydrogen, C₁ -C₃ -alkyl, C₁ -C₃ -halogenoalkyl, C₁-C₃ -alkoxy, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃-alkylsulfinyl, C₁ -C₂ -alkoxyethoxy, C₁ -C₃ -alkylsulfonyl, halogen or-NR⁵ R⁶, R³ is hydrogen or C₁ -C₃ -alkyl and Q is a group ##STR5## inwhich R⁴ is hydrogen, C₁ -C₃ -alkyl, C₁ -C₃ -halogenoalkyl, C₁ -C₃-alkoxy, cyclopropyl, C₁ -C₃ -halogenoalkoxy, C₁ -C₃ -alkylthio, C₂ -C₄-alkoxyalkyl, C₃ -C₅ -dialkoxymethyl, halogen or --NR⁵ R⁶, R⁵ and R⁶independently of one another are hydrogen or C₁ -C₃ -alkyl, X is oxygenor sulfur and A is a group ##STR6## in which Y is oxygen, sulfur,--CH=CH--, --NR⁹ -- or --CR¹⁰ =N--, R⁷ is hydrogen, halogen, C₁ -C₃-alkyl, C₁ -C₃ -alkoxy, nitro or trifluoromethyl, R⁸ is hydrogen,halogen, C₁ -C₃ -alkyl, C₁ -C₃ -alkoxy, nitro, --C=CH, or one of thegroups ##STR7## R⁹ and R¹⁰ independently of one another are hydrogen, C₁-C₃ -alkyl or C₂ -C₄ -alkenyl, R¹¹ is hydrogen, C₁ -C₃ -alkyl, C₁ -C₃-halogenoalkyl, C₃ -C₆ -cycloalkyl or C₂ -C₄ -alkoxyalkyl, R¹² is C₁ -C₆-alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkenyloxy, C₂ -C₆ -halogenoalkoxy,C₁ -C₄ -cyanoalkoxy, C₁ -C₆ -alkylthio, C₃ -C₆ -alkenylthio, C₃ -C₆-alkinylthio, C₅ -C₆ -cycloalkoxy, C₂ -C₆ -alkoxyalkoxy or --NR¹⁶ R¹⁷,R¹³ is hydrogen, C₁ -C₃ -alkyl or C₃ -C₄ -al-kenyl, R¹⁴ is hydrogen, C₁-C₃ -alkyl, C₁ -C₃ -cyanoalkyl or C₁ -C₃ -alkoxy, R¹⁵ is C₃ -C.sub. 6-alkinyl, C₂ -C₆ -alkenyl, C₁ -C₆ -alkyl, C₁ -C₄ -halogenoalkyl, C₂ -C₄-halogenoalkenyl or C₁ -C₄ -alkyl, sub-stituted by cyano, methoxy,ethoxy, nitro, C₁ -C₄ -alkoxycarbonyl, methylthio, ethylthio,methylsulfonyl or ethylsulfonyl; or C₃ -C₄ -alkenyl substituted bynitro, cyano, methoxy or ethoxy, R¹⁶ is hydrogen, C₁ -C₃ -alkyl or C₃-C₄ -alkenyl, R¹⁷ is hydrogen, C₁ -C₃ -alkyl, C₁ -C₃ -cyanoalkyl or C₁-C₃ -alkoxy, R¹⁸ is C₁ -C₃ -alkyl and C₁ -C₃ -halogenoalkyl, W is oxygenor sulfur, Z is oxygen, sulfur, --SO-- or --SO₂ -- and m is the numberzero or one, and the salts of these compounds.

Triazine compounds and pyrimidine compounds with a herbicidal action aregenerally known. Such compounds with a herbicidal and plantgrowth-regulating action have recently been described, for example inPublished European patent applications 44,807, 44,808 and 126,711.

In the definitions, alkyl is to be understood as meaning straight-chainor branched alkyl; for example: methyl, ethyl, n-propyl, i-propyl or thefour isomers of butyl.

Alkoxy is to be understood as meaning: methoxy, ethoxy, n-propyloxy,i-propyloxy or the four isomers of butyloxy but in particular methoxy,ethoxy or i-propyloxy.

Examples of alkylthio are methylthio, ethylthio, n-propylthio,i-propylthio and the four isomers of butylthio, but in particularmethylthio and ethylthio.

Halogen itself and as part of a substituent, such as in halogenoalkoxy,halogenoalkylthio or halogenoalkyl, is to be understood as meaningfluorine, chlorine or bromine, but preferably fluorine or chlorine.Halogenoalkyl itself or as part of halogenoalkoxy or halogenoalkylthiois as a rule chloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl,1,1,2,2-tetrafluoroethyl, pentafluoroethyl,1,1,2-trifluoro-2-chloroethyl, 2,2,2-trifluoro-1,1,-dichloroethyl,pentachloroethyl, 3,3,3-trifluoropropyl, 2,3-dichloropropyl or1,1,2,3,3,3-hexafluoropropyl, but in particular fluoromethyl,chloromethyl, difluoromethyl or trifluoromethyl.

Examples of alkoxyalkyl are: methoxymethyl, methoxyethyl, methoxypropyl,ethoxyethyl, ethoxymethyl and propyloxymethyl. Examples of alkoxyalkoxyare: methoxymethoxy, methoxyethoxy, methoxypropyloxy, ethoxymethoxy,ethoxyethoxy and propyloxymethoxy. Alkylene groups in the context of thedefinition under formula I are ethylene, propylene, butylene,1-methylethylene, 1-ethylethylene, 2-methylbutylene or 1-methylbutylene.Dialkoxymethyl is preferably dimethoxymethyl or diethoxymethyl.

The invention also relates to the salts which the compounds of theformula I can form with amines, alkali metal and alkaline earth metalbases or quaternary ammonium bases.

Preferred alkali metal and alkaline earth metal hydroxides assalt-forming agents are the hydroxides of lithium, sodium, potassium,magnesium or calcium, but in particular those of sodium or potassium.

Examples of amines which are suitable for salt formation are primary,secondary and tertiary aliphatic and aromatic amines, such asmethylamine, ethylamine, propylamine, i-propylamine, the four isomericbutylamines, dimethylamine, diethylamine, diethanolamine, dipropylamine,diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine,trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine,quinoline and i-quinoline, but in particular ethyl-, propyl-, diethyl-or triethylamine, and especially iso-propylamine, diethanolamine and1,4-diazabicyclo[2.2.2]octane.

Examples of quaternary ammonium bases are in general the cations ofhalogenoammonium slats, for example the tetramethylammonium cation, thetetraethylammonium cation or the trimethylethylammonium cation, oralternatively the ammonium cation.

Preferred compounds of the formula I are those in which either (a) X isoxygen, or (b) A is the group ##STR8## or (c) R³ is hydrogen, or (d) R¹is methyl or ethyl, R² is hydrogen, methoxy or methyl and E is the group═CR⁴ --, or (e) R¹ is methyl or ethyl, R² is methoxy, ethoxy,methylthio, dimethylamino, methyl, trifluoromethyl,2,2,2-trifluoroethoxy or ethyl and E is nitrogen.

Preferred compounds of group (b) are those in which R⁷ is hydrogen andR⁸ is methoxycarbonyl, ethoxycarbonyl, dimethylaminosulfonyl, ethoxy,propoxy, difluoromethoxy, trifluoromethyl, chloroethoxy, methoxyethoxy,2,2,2-trifluoroethoxy, 1,2-dichlorovinyloxy, nitro, fluorine, chlorine,bromine, methyl, methylthio, difluoromethylthio, chloroethylthio,--O--SO₂ CH₃, allyloxy or methoxy.

Preferred compounds of group (d) are those in which R⁴ is chlorine,bromine, methoxy, ethoxy, methyl, ethyl, methylthio, dimethylamino,trifluoromethyl or 2,2,2-trifluoroethoxy.

Particularly preferred sub-groups of compounds of the formula I areformed from those compounds in which either R¹ is methyl or ethyl, R² ishydrogen, methoxy or methyl, R³ is hydrogen, X is oxygen, A is the group##STR9## R⁷ is hydrogen, R⁸ is methoxycarbonyl, ethoxycarbonyl,dimethylaminosulfonyl, methoxy, ethoxy, difluoromethoxy,trifluoromethyl, chloroethoxy, methoxyethoxy, 2,2,2-trifluoroethoxy,1,2-dichlorovinyloxy, nitro, fluorine, chlorine, bromine, methyl,methylthio, difluoromethylthio, chloroethylthio, --O--SO₂ CH₃ orallyloxy, E is the group ═CR⁴ --and R⁴ is chlorine, bromine, methoxy,ethoxy, methyl, ethyl, methylthio, dimethylamino, trifluoromethyl or2,2,2-trifluoroethoxy; or in which R¹ is methyl or ethyl, R² is methoxy,ethoxy, methylthio, dimethylamino, methyl, trifluoromethyl,2,2,2-trifluoroethoxy or ethyl, R³ is hydrogen, E is nitrogen, X isoxygen, A is the group ##STR10## R⁷ is hydrogen and R⁸ ismethoxycarbonyl, ethoxycarbonyl, dimethylaminosulfonyl, methoxy, ethoxy,difluoromethoxy, trifluoromethyl, chloroethoxy, methoxyethoxy,2,2,2-trifluoroethoxy, 1,2-dichlorovinyloxy, nitro, fluorine, chlorine,bromine, methyl, methylthio, difluoromethylthio, chloroethylthio,--O--SO₂ CH₃ or allyloxy.

Preferred individual compounds of the formula I which may be mentionedare:6-[3-(2-methoxycarbonylphenylsulfonyl)ureido]-5-chloro-1-methylpyrazine-2-oneand6-[3-(2-methoxycarbonylphenylsulfonyl)-ureido]-3-methoxy-4-methyl-1,2,4-triazin-5-one.

The compounds of the formula I are in general prepared by the followingmethods.

According to a first process, the compounds of the formula I areobtained by reacting an aminopyrazinone or aminotriazinone of theformula II ##STR11## in which R¹, R², R³ and E are as defined underformula I, with a sulfonyl isocyanate of the formula III

    X═C═N--SO.sub.2 --A                                (III)

in which A and X are as defined under formula I.

According to a second process, the compounds of the formula I areobtained by reacting an aminopyrazinone or aminotriazinone of theformula II with a sulfonyl carbamate of the formula IV ##STR12## inwhich A and X are as defined under formula I and R is phenyl, alkyl orsubstituted phenyl, in the presence of a base.

Finally, the compounds of the formula I can also be obtained by reactinga carbamate of the formula V ##STR13## in which R¹, R², R³, E and X areas defined under formula I and R is phenyl, alkyl or substituted phenyl,with a sulfonamide of the formula VI

    H.sub.2 N--SO.sub.2 --A                                    (VI)

in which A is as defined under formula I, in the presence of a base.

If desired, the resulting ureas of the formula I can be converted intoaddition salts by means of amines, alkali metal or alkaline earth metalhydroxides or quaternary ammonium bases. This is effected, for example,by reaction with the equimolar amount of a base and evaporation of thesolvent.

The reactions to give compounds of the formula I are advantageouslycarried out in aprotic inert organic solvents. Such solvents arehydrocarbons, such as benzene, toluene, xylene or cyclohexane, carbontetrachloride, chlorobenzene, ethers, such as diethyl ether, ethyleneglycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuranor dioxane, nitriles, such as acetonitrile or propionitrile, or amides,such as dimethylformamide, diethylformamide or N-methylpyrrolidinone.The reaction temperatures are preferably between -20° and +120° C. Thereactions of the coupling processes in general proceed as slightlyexothermic reactions and can be carried out at room temperature. For thepurpose of shortening the reaction time or of initiating the reaction,it is expedient to heat the reaction mixture up to its boiling point fora short time. The reaction times can also be shortened by addition of afew drops of a base as a reaction catalyst. Particularly suitable basesare tertiary amines, such as trimethylamine, triethylamine,quinuclidine, 1,4-diazabicyclo[2.2.2]-octane,1,5-diazabicyclo[4.3.0]non-5-ene or 1,8-diazabicyclo[5.4.0]undec-7ene.However, inorganic bases, such as hydrides, such as sodium or calciumhydride, hydroxides, such as sodium and potassium hydroxide, carbonates,such as sodium and potassium carbonate, or bicarbonates, such aspotassium and sodium bicarbonate, can also be used as the bases.

The end products of the formula I can be isolated by concentrating themixture and/or evaporating off the solvent and can be purified byrecrystallization or trituration of the solid residue in solvents inwhich they are not readily soluble, such as ethers, aromatichydrocarbons or chlorinated hydrocarbons.

The intermediate products of the formulae III, IV and Vi and theirpreparation are known from the literature. These substances aredescribed, for example, in U.S. Pat. No. 4,127,405, U.S. Pat. No.4,305,884, European Pat. A-13,480, European Pat. A-44,807 European Pat.A-44,808.

The aminopyrazinones and aminotriazinones of the formula II used asstarting materials are known in some cases from the literature. Thenovel compounds of the formula II have been developed and preparedspecifically for the preparation of the active substances according tothe invention. They therefore form part of the present invention. Thesecompounds are those of the formula II, with the proviso that R³ is C₁-C₃ -alkyl if (a) at the same time E is nitrogen, R¹ is methyl and R² ismethyl or methylthio; or (b) at the same time R¹ is methyl, R² ishydrogen and E is the group ═CCL-- ═CH--.

The carbamates of the formula V are obtained from the amino compounds ofthe formula II by reaction with carbonic acid derivatives of the formulaVII

    (RO).sub.2 C═X                                         (VII)

in which R and X are as defined above.

The carbonic acid derivatives of the formula VII are known and some ofthem are commercially available.

The starting materials of the formula II can be prepared by variousmethods depending on the substitution sought.

Thus, the aminotriazinones of the sub-formula IIa ##STR14## in which R¹and R₃ are as defined under formula I and R² is C₁ -C₃ -alkyl, C₁ -C₃-halogenoalkyl, hydrogen or C₁ -C₃ -alkylthio, are obtained by reactinga compound of the formula VIII ##STR15## in which R¹ and R² are asdefined under formula IIa, with an oxalic acid derivative of the formulaIX ##STR16## in which R³ is as defined under formula II and R is alkylor aryl.

Aminotriazinone syntheses of this type are described in Liebig's Ann.Chem. 1984, 283-295. The intermediate products VIII and IX are known orcan be obtained by processes analogous to published processes.

The aminotriazinones of the sub-formula IIa in which R¹ and R³ are asdefined under formula I and R² is C₁ -C₃ -alkoxy, C₂ -C₃-halogenoalkoxy, halogen or --NR⁵ R⁶ are obtained by oxidizingaminotriazinones of the formula IIa in which R² is C₁ -C₃ -alkylthiowith suitable oxidizing agents, such as H₂ O₃ or Cl₂, and subsequentlyreacting the products with nucleophiles of the formula X

    H--R                                                       (X)

in which R is C₁ -C₃ -alkoxy, C₂ -C₃ -halogenoalkoxy or --NR⁵ R⁶, inappropriate in the presence of a base.

The aminopyrazinones of the sub-formula IIB ##STR17## in which R¹, R²,R³ and R⁴ are as defined under formula I, are prepared by reacting a2-amino-pyrazinone of the formula XI ##STR18## in which R², R³ and R⁴are as defined under formula I, with alkylating agents, for examplealkyl halides, alkyl tosylates or dialkyl sulfates, in the presence of abase. Alkylations of this type are described, for example, in J. Chem.Soc. 1965, 6681. Starting substances of the formula XI are known or canbe obtained by methods analogous to published methods.

Aminopyrazines of the formula IIb are also obtained by reactingpyrazinones of the formula XII ##STR19## in which R¹, R² and R⁴ are asdefined under formula I and X is Cl, Br or OSO₂ CF₃, with an amine ofthe formula XIII

    H.sub.2 N--R.sup.#                                         (XIII)

in which R³ is hydrogen or C₁ -C₃ -alkyl. Syntheses of this type aredescribed in J. Het. Chem. 20. 919-923 (1983).

Pyrazinones of the sub-formula XIIa ##STR20## in which R² is hydrogen orC₁ -C₄ -alkyl, R⁴ is --NR⁵ R⁶, C₁ -C₃ -alkylthio, C₁ C₃ -alkoxy or C₂-C₃ -halogenoalkoxy and R¹ and X are as defined in formula XII, areprepared by reacting pyrazinones of the formula XIV ##STR21## in whichR¹, R² and R⁴ are as defined in formula XIIa, with (CF₃ SO₂)O, PCl₅,POCl₃, POBr₃, (COCl)₂ or (COBr)₂, if appropriate in the presence of abase, in inert solvents, such as, for example, dichloromethane,acetonitrile, chloroform or carbon tetrachloride.

Pyrazinones of the formula XIV or alkali metal salts thereof areobtained by acylating aminoalkylcyanides of the formula XV ##STR22## inwhich R¹ is C₁₈ -C₄ -alkyl and R² is hydrogen or C₁ -C₃ -alkyl, withoxalic acid chlorides of the formula XVI ##STR23## in which R is C₁ -C₃-alkyl, and subsequently reacting the products with nucleophiles of theformula XVII,

    H--R.sup.4                                                 (XVII)

in which R⁴ is as defined in formula XIIa, if appropriate in thepresence of a base. ##STR24## in which R¹ is C₁ -C₄ -alkyl, R² ishydrogen or C₁ -C₃ -alkyl and X and R⁴ are chlorine or bromine, areobtained by reacting aminoalkyl cyanides of the formula XV with oxalylchloride or bromide.

Syntheses of this type and pyrazinones of the formula XIIb are describedin J. Het. Chem. 20, 919-923 (1983).

The pyrazinones of the sub-formula XIIc ##STR25## in which R², R² and R⁴are as defined in formula I and X is chlorine or bromine, are obtainedby reacting pyrazinones of the formula XVIII ##STR26## in which R², R⁴and X are as defined under formula XIIc, with alkylating agents, forexample alkyl halides, alkyl tosylates or dialkyl sulfates, in thepresence of a base. The starting substances of the formula XVIII areknown or can be obtained by methods of analogous to published methods.

The active substances of the formula I are stable compounds. Theirhandling requires no precautionary measures.

When applied in relatively small amounts, the compounds of the formula Iare distinguished by good selective growth-inhibiting and selectiveherbicidal properties, which makes them excellently suitable for use incrops of useful plants, in particular in cereals, rice, cotton, soybeanand maize. In some cases, weeds which were previously to be controlledonly with total herbicides are also damaged.

The mode of action of these active substances is unusual. Many of themare translocatable, i.e. they are taken up by the plant and transportedto other points, where they can act. It is thus possible, for example,to damage perennial weeds down to the roots by surface treatment. Incontrast to other herbicides and growth regulators, the novel compoundsof the formula I already act when very low amounts are applied.

The compounds of the formula I also have potent plant growth-regulating,in particular plant growth-inhibiting, properties. The growth of bothmonocotyledons and dicotyledons is impaired.

Thus, for example, the growth of leguminosae frequently planted as covercrops in agriculture in tropical regions can be selectively inhibited bythe compounds of the formula I, so that although soil erosion betweenthe crop plants is prevented, the cover crops cannot become competitionfor the crop.

For many crop plants, an inhibition of vegetative growth allows denserplanting of the crop, so that an increased harvest, based on the soilsurface, can be achieved.

Another mechanism of increasing yield with growth inhibitors is based onthe fact that the nutrients benefit blossom and fruit formation to agreater degree, whilst vegetative growth is restricted.

When larger amounts of active substances of the formula I are applied,the development of all the plants tested is damaged to the extent thatthey die.

The invention also relates to herbicidal and plant growth-regulatingcompositions which contain a novel active substance of the formula I,and to processes for pre- and post-emergence weed control and forinhibition of the growth of monocotyledon and dicotyledon plants, inparticular grasses, tropical cover crops and tobacco side shoots.

The compounds of the formula I are used in non-modified form or,preferably, as compositions together with the auxiliaries customary informulation technology, and are therefore processed in a known manner toemulsion concentrates, directly sprayable or dilutable solutions,diluted emulsions, wettable powders, soluble powders, dusts, granules orencapsulations in, for example, polymeric substances. The methods ofuse, such as spraying, misting, dusting, scattering or watering, likethe nature of the agent, are chosen according to the intended aims andthe given circumstances.

The formulations, i.e. the compositions, formulations or combinationscontaining the active substance of the formula I and if appropriate asolid or liquid additive are prepared in a known manner, for example byintimate mixing and/or grinding of the active substances with extenders,for example with solvents, solid carriers and if appropriatesurface-active compounds (surfactants).

Possible solvents are: aromatic hydrocarbons, preferably C₈ to C₁₂fractions, for example xylene mixtures or substituted naphthalenes,phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatichydrocarbons, such as cyclohexane or paraffins, alcohols and glycols andethers and esters thereof, such as ethanol, ethylene glycol or ethyleneglycol monomethyl or monoethyl ether, ketones, such as cyclohexanone,highly polar solvents, such as N-methyl-2-pyrrolidone, dimethylsulfoxideor dimethylformamide, and if appropriate epoxidized vegetable oils, suchas epoxidized coconut oil or soybean oil; or water.

The solid carriers used, for example for dusts and dispersible powders,are as a rule natural rock powders, such as calcite, talc, kaolin,montmorillonite or attapulgite. Highly disperse silicic acid or highlydisperse absorbent polymers can also be added to improve the physicalproperties. Possible granular adsorptive granule carriers are poroustypes, for example pumice, crushed brick, sepiolite or bentonite, andpossible non-adsorptive carrier materials are, for example, calite orsand. A large number of pre-granulated materials of inorganic or organicnature, such as, in particular, dolomite or comminuted plant residues,can moreover be used.

Possible surface-active compounds are, depending on the nature of theactive substance of the formula I to be formulated, nonionic, cationicand/or anionic surfactants with good emulsifying, dispersing and wettingproperties. Surfactants are also to be understood as meaning surfactantmixtures.

Suitable anionic surfactants can be either so-called water-soluble soapsor water-soluble synthetic surface-active compounds.

Soaps which may be mentioned are the alkali metal, alkaline earth metalor substituted or unsubstituted ammonium salts of higher fatty acids(C₁₀ -C₂₂), for example the Na or K salts of oleic or stearic acid, orof naturally occurring fatty acid mixtures which can be obtained, forexample, from coconut oil or tallow oil. Fatty acid methyl-taurine saltsmay furthermore also be mentioned.

However, so-called synthetic surfactants, in particular fattysulfonates, fatty sulfates, sulfonated benzimidazole derivatives oralkylarylsulfonates, are more frequently used.

The fatty sulfates or sulfonates are as a rule in the form of alkalimetal, alkaline earth metal or substituted or unsubstituted ammoniumsalts and have an alkyl radical having 8 to 22 C atoms, alkyl alsoincluding an alkyl part of acyl radicals, for example the Na or Ca saltof the ligninsulfonic acid, of dodecylsulfuric acid ester or of a fattyalcohol sulfate mixture prepared from naturally occurring fatty acids.The salts of sulfuric acid esters and sulfonic acids of fattyalcohol-ethylene oxide adducts are also included here. The sulfonatedbenzimidazole derivatives preferably contain 2-sulfonic acid groups anda fatty acid radical having 8 to 22 C atoms. Alkylarylsulfonates are,for example, the Na, Ca or triethanolamine salts ofdodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of anaphthalenesulfonic acid-formaldehyde condensation product.

Corresponding phosphates, for example the salts of the phosphoric acidester of a p-nonylphenol-(4-14)-ethylene oxide adduct or phospholipids,are furthermore also suitable.

Possible nonionic surfactants are in particular polyglycol etherderivatives of aliphatic or cycloaliphatic alcohols, saturated orunsaturated fatty acids and alkylphenols, which can contain 3 to 10glycol ether groups and 8 and 20 carbon atoms in the (aliphatic)hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of thealkylphenols.

Other suitable nonionic surfactants are the water-soluble adducts,containing 20 to 250 ethylene glycol ether groups and 10 to 100propylene glycol ether groups, of polyethylene oxide on polypropyleneglycol, ethylenediaminopolypropylene glycol and alkylpolypropyleneglycol having 1 to 10 carbon atoms in the alkyl chain, the compoundsmentioned usually containing 1 to 5 ethylene glycol units per propyleneglycol unit.

Examples which may be mentioned of nonionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene-polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylenesorbitan trioleate, are furthermore also possible.

The cationic surfactants are in particular quaternary ammonium saltswhich contain at least one alkyl radical with 8 to 22 C atoms as the Nsubstituent and lower free or halogenated alkyl, benzyl or lowerhydroxyalkyl radicals as further substituents. The salts are preferablyin the form of halides, methylsulfates or ethylsulfates, for examplestearyltrimethylammonium chloride orbenzyldi(2-chloroethyl)-ethylammonium bromide.

Surfactants which are customary in formulation technology are described,inter alia, in the following publications: "McCutcheon's Detergents andEmulsifiers Annual" MC Publishing Corp., Ridgewood, New Jersey, 1981; H.Stache, "Tensid-Taschenbuch (Surfactant handbook)", 2nd edition, C.Hanser Verlag, Munich, Vienna, 1981; and M. and J. Ash. "Encyclopedia ofSurfactants", volume I-III, Chemical Publishing Co., New York,1980-1981.

The agrochemical formulations as a rule contain 0.1 to 95%, inparticular 0.1 to 80%, of active substance of the formula I, 1 to 99.9%of a solid or liquid additive and 0 to 25%, in particular 0.1 to 25%, ofa surfactant.

Preferred formulations have, in particular, the following compositions:(%=percent by weight).

    ______________________________________                                        Emulsifiable concentrates:                                                    Active substance:                                                                            1 to 20%, preferably                                                                          5 to 10%                                       Surface-active agent:                                                                        5 to 30%, preferably                                                                          10 to 20%                                      Liquid carrier:                                                                              50 to 94%, preferably                                                                         70 to 85%                                      Dusts:                                                                        Active substance:                                                                            0.1 to 10%, preferably                                                                        0.1 to 1%                                      Solid carrier: 99.9 to 90%, preferably                                                                       99.9 to 99%                                    Suspension concentrates:                                                      Active substance:                                                                            5 to 75%, preferably                                                                          10 to 50%                                      Water:         94 to 24%, preferably                                                                         88 to 30%                                      Surface-active agent:                                                                        1 to 40%, preferably                                                                          2 to 30%                                       Wettable powder:                                                              Active substance:                                                                            0.5 to 90%, preferably                                                                        1 to 80%                                       Surface-active agent:                                                                        0.5 to 20%, preferably                                                                        1 to 15%                                       Solid carrier: 5 to 95%, preferably                                                                          15 to 90%                                      Granules:                                                                     Active substance:                                                                            0.5 to 30%, preferably                                                                        3 to 15%                                       Solid carrier: 99.5 to 70%, preferably                                                                       97 to 85%.                                     ______________________________________                                    

Whilst concentrated compositions are preferred rather as commercialgroups, the end user as a rule uses dilute compositions. The use formscan be diluted down to 0.001% of active substance. The amounts appliedare as a rule 0.01 to 10 kg of active substance/ha, preferably 0.025 to5 kg of active substance/ha.

The compositions can also contain further additives, such asstabilizers, foam suppressants, viscosity regulators, binders,tackifiers and fertilizers or other active substances, in order toachieve special effects.

PREPARATION EXAMPLES Example H1:3-[3-(2-Methoxycarbonylphenylsulfonyl)-ureido]-5-chloro-1-methylpyrazin-2-one.(Compound 1.01)

A mixture of 2.41 g of 2-methoxycarbonylphenylsulfonyl isocyanate, 1.6 gof 3-amino-5-chloro-1-methylpyrazin-2-one and 40 ml of absolute dioxaneis refluxed for 3 hours. The reaction mixture is evaporated to drynessand the residue is crystallized by treatment with acetone. 3.8 g of3-[3-[(2-methoxycarbonylphenylsulfonyl)-ureido]-5-chloro-1-methylpyrazin-2-onewith a melting point of 213°-214° C. are thus obtained.

Example H2:6-[3-(2-Methoxycarbonylphenylsulfonyl)-ureido]-4-methyl-3-methylthio-1,2,4-triazin-5-one(Compound 7.06)

3.42 g of 6-amino-4-methyl-3-methylthio-1,2,4-triazin-5-one aresuspended in 100 ml of absolute dioxane, and 4.99 g of2-methoxycarbonylphenylsulfonyl isocyanate are added at roomtemperature. The reaction proceeds slightly exothermically. After areaction time of one hour at room temperature, the reaction has ended.The precipitate which has separated out is filtered off and washed witha small amount of dioxane. After drying, 6.0 g of6-[3-(2-methoxycarbonylphenylsulfonyl)-ureido]-4-methyl-3-methylthio-1,2,4-triazin-5-onewith a melting point of 186° C. are thus obtained.

Example H3: 3-Amino-1,6-dimethylpyrazin-2-one (Compound 14.12)

8.87 g of dimethyl sulfate are added dropwise to a mixture of 8.13 g of3-amino-6-methylpyrazin-2-one and 72 ml of 1 N sodium hydroxide solutionat room temperature. After the mixture has been stirred at 20°-25° C.for 15 hours, the precipitate is filtered off, the filtrate isconcentrated to one quarter of the volume and the concentrate isextracted with ethyl acetate. 1.7 g of 3-amino-1,6-dimethylpyrazin-2-onewith a melting point of 217°-219° C. are obtained by washing withsaturated sodium chloride solution, drying with sodium sulfate andconcentrating the organic phase.

Example H4: 6-Amino-4-methyl-3-methylsulfinyl-1,2,4-triazin-5-one(Compound 13.25)

1.7 g of 6-amino-4-methyl-3-methylthio-1,2,4-triazin-5-one are dispersedin 200 ml of methylene chloride, and 1.8 g of 3-chloroperbenzoic acidare added in portions at 15°-20° C. A clear yellow solution is therebyformed and is evaporated at 40° C. in vacuo. The solid residue istreated with ethyl acetate, whereupon the 3-chlorobenzoic acid formed inthe reaction dissolves completely. The undissolved pure product isfiltered off to give 1.1 g of6-amino-4-methyl-3-methylsulfinyl-1,2,4-triazin-5-one with a meltingpoint of 189° C. (decomposition).

Example H5: 6-Amino-3-methoxy-4-methyl-1,2,4-triazin-5-one (Compound13.03)

4.1 g of 6-amino-4-methyl-3-methylsulfinyl-1,2,4-triazin-5-one aresuspended in 50 ml of absolute methanol, and 4.3 ml of 30% strengthmethanolic sodium methylate solution are added at room temperature. Thereaction proceeds slightly exothermically and the temperature rises to35° C. The solution is then stirred at 50° C. for 30 minutes, whereupona colourless precipitate separates out of the clear yellow solution. Thereaction mixture is evaporated and the residue is taken up in ethylacetate and ice-water. The organic phase is separated off, dried withmagnesium sulfate and evaporated. The residue is washed with a littlemethanol and dried. 1.6 g of6-amino-4-methyl-3-methoxy-1,2,4-triazin-5-one with a melting point of198°-199° C. are obtained in this manner.

Example H6:3-[3-(2-Chloro-pyridin-3-ylsulfonyl)ureido]-5-chloro-1-methylpyrazin-2-one(Compound 5.01) (a) PhenylN-(5-chloro-1-methylpyrazin-2-on-3-yl)-carbamate

A solution of 9.4 g of diphenyl carbonate and 65 ml of dimethylformamideis allowed to run into a mixture of 1.9 g of a 55% sodium hydridedispersion and 20 ml of dimethylformamide at 10°-15° C. 6.4 g of3-amino-5-chloro-1-methylpyrazin-2-one are then introduced in portionsat the same temperature and the mixture is stirred for a further 45minutes. The mixture is filtered, the filtrate is poured into a mixtureof 270 ml of ethyl aceate, 270 ml of ice-water and 42 ml of 7%hydrochloric acid, the organic phase is washed with water and sodiumchloride solution and dried over sodium sulfate, the solution isconcentrated and the product which has precipitated out is filtered offto give 6.5 g of phenylN-(5-chloro-1-methylpyrazin-2-on-3-yl)-carbamate.

(b) A solution of 1.52 g of 1,8-diazabicyclo-[5.4.0]-un-dec-7-ene and 10ml of dioxane is added dropwise to a mixture of 1.93 g of2-chloro-pyridin-3-yl-sulfonamide and 2.8 g of phenylN-5-chloro-(1-methylpyrazin-2-on-3-yl)-carbamate. The reaction mixtureis then stirred at 20°-25° C. for 15 hours. It is poured into water, 10%hydrochloric acid is added dropwise to a pH of 4.5 and the precipitateformed is filtered off, washed with water and dried to give 3.2 g of3-[3-(2-chloro-pyridin-3-ylsulfonyl)ureido]-5-chloro-1-methylpyrazin-2-oneof melting point 202°-203° C. (decomposition).

Example H7: 3-Amino-5-methoxy-1-methylpyrazin-2-one (Compound 14.03) (a)N-Cyanomethyl-N-methyl-methoxalylamide.

A solution of 15.8 g of pyridine and 20 ml of methylene chloride isadded dropwise to a mixture of 12.3 g of methoxalyl chloride, 15.8 g ofmethylaminoacetonitrile hydrochloride and 80 ml of methylene chloride.The mixture is then stirred at 20°-25° C. for 3 hours. 50 ml of waterare subsequently added and the organic phase is washed with 5%hydrochloric acid, water and sodium chloride solution in succession. Themixture is dried and evaporated to give 14,1 g ofN-cyanomethyl-N-methyl-methoxalylamide.

(b) 3-Hydroxy-5-methoxy-1-methylpyrazin-2-one

33.2 g of 30% methanolic sodium methylate solution are allowed to runinto a solution of 14.4 g of N-cyanomethyl-N-methyl-methoxalylamide and200 ml of absolute methanol. The mixture is then stirred at 55°-60° C.for 6 hours and subsequently evaporated to dryness. The residue isstirred with ice-water and brought to pH 6.5 by dropwise addition of 30%hydrochloric acid. The product is filtered off, washed with ice-waterand dried to give 8.3 g of 3-hydroxy-5-methoxy-1-methylpyrazin-2-one ofmelting point 201°-204° C.

(c) 5-Methoxy-1-methyl-3-trifluoromethylsulfonyloxypyrazin-2-one

62 g of trifluoromethanesulfonic acid anhydride are added dropwise to asuspension of 31.2 g of 3-hydroxy-5-methoxy-1-methylpyrazin-2-one, 15.8g of pyridine and 500 ml of methylene chloride at 20°-25° C. Thesolution formed is stirred at 20°-25° C. for a further 2 hours, and 200ml of ice-water are then added. The organic phase is separated off,washed with 10% sodium bicarbonate solution and water, dried over sodiumsulfate and evaporated to give 39.5 g of5-methoxy-1-methyl-3-trifluoromethylsulfonyloxy-pyrazin-2-one of meltingpoint 107°-108° C.

(d) 4.7 g of ammonia are passed into a solution of 28.8 g of5-methoxy-1-methyl-3-trifluoromethyl-sulfonyloxy-pyrazin-2-one and 100ml of tetrahydrofuran at 5° to 10° C. in the course of 1.5 hours. A darksuspension is formed and is stirred at 0° to +5° C. for 2 hours. Theprecipitate is filtered off and washed with cold tetrahydrofuran to give10.6 g of 3-amino-5-methoxy-1-methyl-pyrazin-2-one of melting point166°-167° C.

Example H8: 1-Ethyl-3-amino-5-bromopyrazin-2-one (Compound 14.16) (a)3,5-Dibromo-pyrazin-2-one.

A solution of 12.65 g of 2-amino-3,5-dibromo-pyrazine and 18.5 ml of 96%sulfuric acid is added dropwise to a solution of 3.45 g of sodiumnitrite and 27.5 ml of 96% sulfuric acid at 0° to 5° C. The mixture isthen allowed to warm to 20° C. in the course of 2 hours and is stirredat 20°-25° C. for a further 15 hours. The reaction mixture is pouredinto ice and the product is filtered off, washed with ice-water anddried to give 5.8 g of 3,5-dibromo-pyrazin-2-one.

(b) 1-Ethyl-3,5-dibromo-pyrazin-2-one

6.2 g of 3,5-dibromo-pyrazin-2-one are suspended in a mixture of 38 mlof water, 11.1 ml of 2 N sodium hydroxide solution and 0.5 g of sodiumcarbonate. 4.3 g of diethyl sulfate are then added dropwise at 20°-25°C. and the mixture is subsequently stirred at the same temperature for15 hours. The product is filtered off at 0° C., washed with ice-waterand dried to give 4.6 g of 1-ethyl-3,5-dibromo-pyrazin-2-one.

(c) A mixture of 4.6 g of 1-ethyl-3,5-dibromopyrazin-2-one, 9.6 ml ofdioxane and 6.4 ml of 30% ammonia is stirred at 20°-25° C. for 15 hours.The product is filtered off and washed with alcohol and ether to give1.3 g of 1-ethyl-3-amino-5-bromo-pyrazin-2-one with a melting point of227°-230° C.

The intermediates and end products listed in the following tables 1 to14 are obtained analogously.

                                      TABLE 1                                     __________________________________________________________________________     ##STR27##                                                                                                                       Melting                    Compound                                          point                       No.    R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                          R.sup.4   R.sup.7                                                                            R.sup.8      X [°C.]                __________________________________________________________________________    1.01   CH.sub.3                                                                           H    H  Cl        H    COOCH.sub.3  O 213-214                     1.02   CH.sub.3                                                                           H    H  Br        H    COOCH.sub.3  O 206-208                     1.03   CH.sub.3                                                                           H    H  H         H    COOCH.sub.3  O 208-209                     1.04   CH.sub.3                                                                           H    H  CH.sub.3  H    COOCH.sub.3  O                             1.05   CH.sub.3                                                                           H    H  OCH.sub.3 H    COOCH.sub.3  O 172-173                     1.06   CH.sub.3                                                                           H    H  N(CH.sub.3).sub.2                                                                       H    COOCH.sub.3  O                             1.07   CH.sub.3                                                                           H    H  SCH.sub.3 H    COOCH.sub.3  O                             1.08   CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    COOCH.sub.3  O                             1.09   CH.sub.3                                                                           H    H  OCH.sub.2CF.sub.3                                                                       H    COOCH.sub.3  O                             1.10   CH.sub.3                                                                           H    H  CF.sub.3  H    COOCH.sub.3  O                             1.11   CH.sub.3                                                                           CH.sub.3                                                                           H  CH.sub.3  H    COOCH.sub.3  O 198-199                     1.12   CH.sub.3                                                                           CH.sub.3                                                                           H  H         H    COOCH.sub.3  O 192-193                     1.13   CH.sub.3                                                                           CH.sub.3                                                                           H  Cl        H    COOCH.sub.3  O                             1.14   CH.sub.3                                                                           CH.sub.3                                                                           H  OCH.sub.3 H    COOCH.sub.3  O                             1.15   C.sub.2 H.sub.5                                                                    H    H  Cl        H    COOCH.sub.3  O                             1.16   C.sub.2 H.sub.5                                                                    H    H  Br        H    COOCH.sub.3  O 183-186                     1.17   C.sub.2 H.sub.5                                                                    H    H  H         H    COOCH.sub.3  O                             1.18   C.sub.2 H.sub.5                                                                    H    H  CH.sub.3  H    COOCH.sub.3  O                             1.19   C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3 H    COOCH.sub.3  O                             1.20   C.sub.2 H.sub.5                                                                    H    H  N(CH.sub.3).sub.2                                                                       H    COOCH.sub.3  O                             1.21   C.sub.2 H.sub.5                                                                    H    H  SCH.sub.3 H    COOCH.sub.3  O                             1.22   C.sub.2 H.sub.5                                                                    H    H  OC.sub.2 H.sub.5                                                                        H    COOCH.sub.3  O                             1.23   C.sub.2 H.sub.5                                                                    H    H  OCH.sub.2CF.sub.3                                                                       H    COOCH.sub.3  O                             1.24   C.sub.2 H.sub.5                                                                    H    H  CF.sub.3  H    COOCH.sub.3  O                             1.25   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  CH.sub.3  H    COOCH.sub.3  O                             1.26   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  H         H    COOCH.sub.3  O                             1.27   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  Cl        H    COOCH.sub.3  O                             1.28   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  OCH.sub.3 H    COOCH.sub.3  O                             1.29   CH.sub.3                                                                           H    H  Cl        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O 225-226                     1.30   CH.sub.3                                                                           H    H  Br        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.31   CH.sub.3                                                                           H    H  H         H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.32   CH.sub.3                                                                           H    H  CH.sub.3  H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.33   CH.sub.3                                                                           H    H  OCH.sub.3 H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.34   CH.sub.3                                                                           H    H  N(CH.sub. 3).sub.2                                                                      H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.35   CH.sub.3                                                                           H    H  SCH.sub.3 H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.36   CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.37   CH.sub.3                                                                           H    H  OCH.sub.2CF.sub.3                                                                       H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.38   CH.sub.3                                                                           H    H  CF.sub.3  H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.39   CH.sub.3                                                                           CH.sub.3                                                                           H  CH.sub.3  H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.40   CH.sub.3                                                                           CH.sub.3                                                                           H  H         H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.41   CH.sub.3                                                                           CH.sub.3                                                                           H  Cl        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.42   CH.sub.3                                                                           CH.sub.3                                                                           H  OCH.sub.3 H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.43   C.sub.2 H.sub.5                                                                    H    H  Cl        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.44   C.sub.2 H.sub.5                                                                    H    H  Br        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.45   C.sub.2 H.sub.5                                                                    H    H  H         H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.46   C.sub. 2 H.sub.5                                                                   H    H  CH.sub.3  H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.47   C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3 H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.48   C.sub.2 H.sub.5                                                                    H    H  N(CH.sub.3).sub.2                                                                       H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.49   C.sub.2 H.sub.5                                                                    H    H  SCH.sub.3 H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.50   C.sub.2 H.sub.5                                                                    H    H  OC.sub.2 H.sub.5                                                                        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.51   C.sub.2 H.sub.5                                                                    H    H  OCH.sub.2CF.sub.3                                                                       H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.52   C.sub.2 H.sub.5                                                                    H    H  CF.sub.3  H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.53   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  CH.sub.3  H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.54   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  H         H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.55   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  Cl        H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.56   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  OCH.sub.3 H    SO.sub.2 N(CH.sub.3).sub.2                                                                 O                             1.57   CH.sub.3                                                                           H    H  Cl        H    OC.sub.2 H.sub.5                                                                           O 237-239                     1.58   CH.sub.3                                                                           H    H  Br        H    OC.sub.2 H.sub.5                                                                           O                             1.59   CH.sub.3                                                                           H    H  H         H    OC.sub.2 H.sub.5                                                                           O                             1.60   CH.sub.3                                                                           H    H  CH.sub.3  H    OC.sub.2 H.sub.5                                                                           O                             1.61   CH.sub.3                                                                           H    H  OCH.sub.3 H    OC.sub.2 H.sub.5                                                                           O 197-199                     1.62   CH.sub.3                                                                           H    H  N(CH.sub.3).sub.2                                                                       H    OC.sub.2 H.sub.5                                                                           O                             1.63   CH.sub.3                                                                           H    H  SCH.sub.3 H    OC.sub.2 H.sub.5                                                                           O                             1.64   CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OC.sub.2 H.sub.5                                                                           O                             1.65   CH.sub.3                                                                           H    H  OCH.sub.2CF.sub.3                                                                       H    OC.sub.2 H.sub.5                                                                           O                             1.66   CH.sub.3                                                                           H    H  CF.sub.3  H    OC.sub.2 H.sub.5                                                                           O                             1.67   CH.sub.3                                                                           CH.sub.3                                                                           H  CH.sub.3  H    OC.sub.2 H.sub.5                                                                           O                             1.68   CH.sub.3                                                                           CH.sub.3                                                                           H  H         H    OC.sub.2 H.sub.5                                                                           O                             1.69   CH.sub.3                                                                           CH.sub.3                                                                           H  Cl        H    OC.sub.2 H.sub.5                                                                           O                             1.70   CH.sub.3                                                                           CH.sub.3                                                                           H  OCH.sub.3 H    OC.sub.2 H.sub.5                                                                           O                             1.71   C.sub.2 H.sub.5                                                                    H    H  Cl        H    OC.sub.2 H.sub.5                                                                           O                             1.72   C.sub.2 H.sub.5                                                                    H    H  Br        H    OC.sub.2 H.sub.5                                                                           O                             1.73   C.sub.2 H.sub.5                                                                    H    H  H         H    OC.sub.2 H.sub.5                                                                           O                             1.74   C.sub.2 H.sub.5                                                                    H    H  CH.sub.3  H    OC.sub.2 H.sub.5                                                                           O                             1.75   C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3 H    OC.sub.2 H.sub.5                                                                           O                             1.76   C.sub.2 H.sub.5                                                                    H    H  N(CH.sub.3).sub.2                                                                       H    OC.sub.2 H.sub.5                                                                           O                             1.77   C.sub.2 H.sub.5                                                                    H    H  SCH.sub.3 H    OC.sub.2 H.sub.5                                                                           O                             1.78   C.sub.2 H.sub.5                                                                    H    H  OC.sub.2 H.sub.5                                                                        H    OC.sub.2 H.sub.5                                                                           O                             1.79   C.sub.2 H.sub.5                                                                    H    H  OCH.sub.2CF.sub.3                                                                       H    OC.sub.2 H.sub.5                                                                           O                             1.80   C.sub.2 H.sub.5                                                                    H    H  CF.sub.3  H    OC.sub.2 H.sub.5                                                                           O                             1.81   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  CH.sub.3  H    OC.sub.2 H.sub.5                                                                           O                             1.82   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  H         H    OC.sub.2 H.sub.5                                                                           O                             1.83   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  Cl        H    OC.sub.2 H.sub.5                                                                           O                             1.84   C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  OCH.sub.3 H    OC.sub.2 H.sub.5                                                                           O                             1.85   CH.sub.3                                                                           H    H  Cl        H    OCHF.sub.2   O 204-205                     1.86   CH.sub.3                                                                           H    H  Br        H    OCHF.sub.2   O                             1.87   CH.sub.3                                                                           H    H  H         H    OCHF.sub.2   O                             1.88   CH.sub.3                                                                           H    H  CH.sub.3  H    OCHF.sub.2   O                             1.89   CH.sub.3                                                                           H    H  OCH.sub.3 H    OCHF.sub.2   O 171-172                     1.90   CH.sub.3                                                                           H    H  N(CH.sub.3).sub.2                                                                       H    OCHF.sub.2   O                             1.91   CH.sub.3                                                                           H    H  SCH.sub.3 H    OCHF.sub.2   O                             1.92   CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCHF.sub.2   O                             1.93   CH.sub.3                                                                           H    H  OCH.sub.2CF.sub.3                                                                       H    OCHF.sub.2   O                             1.94   CH.sub.3                                                                           H    H  CF.sub.3  H    OCHF.sub.2   O                             1.95   CH.sub.3                                                                           CH.sub.3                                                                           H  CH.sub.3  H    OCHF.sub.2   O                             1.96   CH.sub.3                                                                           CH.sub.3                                                                           H  H         H    OCHF.sub.2   O                             1.97   CH.sub.3                                                                           CH.sub.3                                                                           H  Cl        H    OCHF.sub.2   O                             1.98   CH.sub.3                                                                           CH.sub.3                                                                           H  OCH.sub.3 H    OCHF.sub.2   O                             1.99   C.sub.2 H.sub.5                                                                    H    H  Cl        H    OCHF.sub.2   O                             1.100  C.sub.2 H.sub.5                                                                    H    H  Br        H    OCHF.sub.2   O                             1.101  C.sub.2 H.sub.5                                                                    H    H  H         H    OCHF.sub.2   O                             1.102  C.sub.2 H.sub.5                                                                    H    H  CH.sub.3  H    OCHF.sub.2   O                             1.103  C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3 H    OCHF.sub.2   O                             1.104  C.sub.2 H.sub.5                                                                    H    H  N(CH.sub.3).sub.2                                                                       H    OCHF.sub.2   O                             1.105  C.sub.2 H.sub.5                                                                    H    H  SCH.sub.3 H    OCHF.sub.2   O                             1.106  C.sub.2 H.sub.5                                                                    H    H  OC.sub.2 H.sub.5                                                                        H    OCHF.sub.2   O                             1.107  C.sub.2 H.sub.5                                                                    H    H  OCH.sub.2CF.sub.3                                                                       H    OCHF.sub.2   O                             1.108  C.sub.2 H.sub.5                                                                    H    H  CF.sub.3  H    OCHF.sub.2   O                             1.109  C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  CH.sub.3  H    OCHF.sub.2   O                             1.110  C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  H         H    OCHF.sub.2   O                             1.111  C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  Cl        H    OCHF.sub.2   O                             1.112  C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           H  OCH.sub.3 H    OCHF.sub.2   O                             1.113  CH.sub.3                                                                           H    H  Cl        H    CF.sub.3     O                             1.114  CH.sub.3                                                                           H    H  Br        H    CF.sub.3     O                             1.115  CH.sub.3                                                                           H    H  H         H    CF.sub.3     O                             1.116  CH.sub.3                                                                           H    H  CH.sub.3  H    CF.sub.3     O                             1.117  CH.sub.3                                                                           H    H  OCH.sub.3 H    CF.sub.3     O                             1.118  CH.sub.3                                                                           H    H  N(CH.sub.3).sub.2                                                                       H    CF.sub.3     O                             1.119  CH.sub.3                                                                           H    H  SCH.sub.3 H    CF.sub.3     O                             1.120  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    CF.sub.3     O                             1.121  CH.sub.3                                                                           H    H  OCH.sub.2CF.sub.3                                                                       H    CF.sub.3     O                             1.122  CH.sub.3                                                                           H    H  CF.sub.3  H    CF.sub.3     O                             1.123  CH.sub.3                                                                           CH.sub.3                                                                           H  CH.sub.3  H    CF.sub.3     O                             1.124  CH.sub.3                                                                           CH.sub.3                                                                           H  H         H    CF.sub.3     O                             1.125  CH.sub.3                                                                           CH.sub.3                                                                           H  Cl        H    CF.sub.3     O                             1.126  CH.sub.3                                                                           CH.sub.3                                                                           H  OCH.sub.3 H    CF.sub.3     O                             1.127  C.sub.2 H.sub.5                                                                    H    H  Cl        H    CF.sub.3     O                             1.128  C.sub.2 H.sub.5                                                                    H    H  Br        H    CF.sub.3     O                             1.129  C.sub.2 H.sub.5                                                                    H    H  H         H    CF.sub.3     O                             1.130  C.sub.2 H.sub.5                                                                    H    H  CH.sub.3  H    CF.sub.3     O                             1.131  C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3 H    CF.sub.3     O                             1.132  C.sub.2 H.sub.5                                                                    H    H  N(CH.sub.3).sub.2                                                                       H    CF.sub. 3    O                             1.133  C.sub.2 H.sub.5                                                                    H    H  SCH.sub.3 H    CF.sub.3     O                             1.134  C.sub.2 H.sub.5                                                                    H    H  OC.sub.2 H.sub.5                                                                        H    CF.sub.3     O                             1.135  C.sub.2 H.sub.5                                                                    H    H  OCH.sub.2CF.sub.3                                                                       H    CF.sub.3     O                             1.136  C.sub.2 H.sub.5                                                                    H    H  CF.sub.3  H    CF.sub.3     O                             1.137  C.sub.2 H.sub.5                                                                    H    H  CH.sub.3  H    CF.sub.3     O                             1.138  C.sub.2 H.sub.5                                                                    H    H  H         H    CF.sub.3     O                             1.139  C.sub.2 H.sub.5                                                                    H    H  Cl        H    CF.sub.3     O                             1.140  C.sub.2 H.sub.5                                                                    H    H  OCH.sub.3 H    CF.sub.3     O                             1.141  C.sub.3 H.sub.7i                                                                   H    H  Cl        H    COOCH.sub.3  O                             1.142  C.sub.3 H.sub.7i                                                                   H    H  CH.sub.3  H    COOCH.sub.3  O                             1.143  C.sub.3 H.sub.7i                                                                   H    H  OCH.sub.3 H    COOCH.sub.3  O                             1.144  CH.sub.3                                                                           H    H  Cl        H    COOCH.sub.3  S                             1.145  CH.sub.3                                                                           H    CH.sub.3                                                                         Cl        H    COOCH.sub.3  O                             1.146  CH.sub.3                                                                           H    C.sub.2 H.sub.5                                                                  Cl        H    COOCH.sub.3  O                             1.147  CH.sub.3                                                                           H    H  Cl        5-OCH.sub.3                                                                        COOCH.sub.3  O                             1.148  CH.sub.3                                                                           H    H  Cl        5-F  COOCH.sub.3  O                             1.149  CH.sub.3                                                                           H    H  Cl        6-Cl COOCH.sub.3  O                             1.150  C.sub.3 H.sub.7i                                                                   H    H  Cl        H    OCHF.sub.2   O                             1.151  C.sub.3 H.sub.7i                                                                   H    H  CH.sub.3  H    OCHF.sub.2   O                             1.152  C.sub.3 H.sub.7i                                                                   H    H  OCH.sub.3 H    OCHF.sub.2   O                             1.153  CH.sub.3                                                                           H    CH.sub.3                                                                         Cl        H    OCHF.sub.2   O                             1.154  CH.sub.3                                                                           H    C.sub.2 H.sub.5                                                                  Cl        H    OCHF.sub.2   O                             1.155  CH.sub.3                                                                           H    H  Cl        5-OCH.sub.3                                                                        OCHF.sub.2   O                             1.156  CH.sub.3                                                                           H    H  Cl        5-F  OCHF.sub.2   O                             1.157  CH.sub.3                                                                           H    H  Cl        5-Cl OCHF.sub.2   O                             1.158  CH.sub.3                                                                           H    H  Cl        H    CHF.sub.2    O                             1.159  CH.sub.3                                                                           H    H  OCH.sub.3 H    CHF.sub.2    O                             1.160  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    CHF.sub.2    O                             1.161  CH.sub.3                                                                           H    H  Cl        H    OCH.sub.3    O                             1.162  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCH.sub.3    O                             1.163  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCH.sub.3    O                             1.164  CH.sub.3                                                                           H    H  Cl        H    OCH.sub.2CH.sub.2 Cl                                                                       O 238-239                     1.165  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCH.sub.2CH.sub.2 Cl                                                                       O                             1.166  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCH.sub.2CH.sub.2 Cl                                                                       O                             1.167  CH.sub.3                                                                           H    H  Cl        H    OCH.sub.2CH.sub.2 OCH.sub.3                                                                O                             1.168  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCH.sub.2CH.sub.2 OCH.sub.3                                                                O                             1.169  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCH.sub.2CH.sub.2 OCH.sub.3                                                                O                             1.170  CH.sub.3                                                                           H    H  Cl        H    OCH.sub.2CF.sub.3                                                                          O                             1.171  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCClCHCl     O                             1.172  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCClCHCl     O                             1.173  CH.sub.3                                                                           H    H  Cl        H    OCClCHCl     O                             1.174  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCH.sub.2CF.sub.3                                                                          O                             1.175  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCH.sub.2CF.sub.3                                                                          O                             1.176  CH.sub.3                                                                           H    H  Cl        H    NO.sub.2     O                             1.177  CH.sub.3                                                                           H    H  OCH.sub.3 H    NO.sub.2     O                             1.178  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    NO.sub.2     O                             1.179  CH.sub.3                                                                           H    H  Cl        H    COOC.sub.2 H.sub.5                                                                         O                             1.180  CH.sub.3                                                                           H    H  OCH.sub.3 H    COOC.sub.2 H.sub.5                                                                         O                             1.181  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    COOC.sub.2 H.sub.5                                                                         O                             1.182  CH.sub.3                                                                           H    H  Cl        H    Cl           O                             1.183  CH.sub.3                                                                           H    H  OCH.sub.3 H    Cl           O                             1.184  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    Cl           O                             1.185  CH.sub.3                                                                           H    H  Cl        H    F            O                             1.186  CH.sub.3                                                                           H    H  OCH.sub.3 H    F            O                             1.187  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    F            O                             1.188  CH.sub.3                                                                           H    H  Cl        H    Br           O                             1.189  CH.sub.3                                                                           H    H  OCH.sub.3 H    Br           O                             1.190  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    Br           O                             1.191  CH.sub.3                                                                           H    H  Cl        H    CH.sub.3     O                             1.192  CH.sub.3                                                                           H    H  OCH.sub.3 H    CH.sub.3     O                             1.193  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    CH.sub.3     O                             1.194  CH.sub.3                                                                           H    H  Cl        H    SCH.sub.3    O                             1.195  CH.sub.3                                                                           H    H  OCH.sub.3 H    SCH.sub.3    O                             1.196  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    SCH.sub.3    O                             1.197  CH.sub.3                                                                           H    H  Cl        H    SCHF.sub.2   O                             1.198  CH.sub.3                                                                           H    H  OCH.sub.3 H    SCHF.sub.2   O                             1.199  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    SCHF.sub.2   O                             1.200  CH.sub.3                                                                           H    H  Cl        H    SCH.sub.2CH.sub.2 Cl                                                                       O                             1.201  CH.sub.3                                                                           H    H  OCH.sub.3 H    SCH.sub.2CH.sub.2 Cl                                                                       O                             1.202  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    SCH.sub.2CH.sub.2 Cl                                                                       O                             1.203  CH.sub.3                                                                           H    H  Cl        H    SO.sub.2CH.sub.3                                                                           O                             1.204  CH.sub.3                                                                           H    H  OCH.sub.3 H    SO.sub.2CH.sub.3                                                                           O                             1.205  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    SO.sub.2CH.sub.3                                                                           O                             1.206  CH.sub.3                                                                           H    H  Cl        H    SO.sub.2C.sub.2 H.sub.5                                                                    O                             1.207  CH.sub.3                                                                           H    H  OCH.sub.3 H    SO.sub.2C.sub.2 H.sub.5                                                                    O                             1.208  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    SO.sub.2C.sub.2 H.sub.5                                                                    O                             1.209  CH.sub.3                                                                           H    H  Cl        H    OCH.sub.2CHCH.sub.2                                                                        O                             1.210  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCH.sub.2CHCH.sub.2                                                                        O                             1.211  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OCH.sub.2CHCH.sub.2                                                                        O                             1.212  CH.sub.3                                                                           H    H  Cl        H    H            O                             1.213  CH.sub.3                                                                           H    H  OCH.sub.3 H    H            O                             1.214  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    H            O                             1.215  CH.sub.3                                                                           H    H  Cl        H    OSO.sub.2 CH.sub.3                                                                         O 239-240                                                                       (decomposition)             1.216  CH.sub.3                                                                           H    H  OCH.sub.3 H    OSO.sub.2 CH.sub.3                                                                         O                             1.217  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OSO.sub.2 CH.sub.3                                                                         O                             1.218  CH.sub.3                                                                           H    H  OCH.sub.3 H    OCH.sub.2 CH.sub.2 Cl                                                                      O 199-200                     1.219  CH.sub.3                                                                           OCH.sub.3                                                                          H  H         H    COOCH.sub.3  O                             1.220  CH.sub.3                                                                           OCH.sub.3                                                                          H  H         H    OCHF.sub.2   O                             1.221  CH.sub.3                                                                           OCH.sub.3                                                                          H  Br        H    COOCH.sub.3  O                             1.222  CH.sub.3                                                                           Cl   H  Cl        H    COOCH.sub.3  O                             1.223  CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H  H         H    COOCH.sub.3  O                             1.224  CH.sub.3                                                                           C.sub.3 H.sub.7                                                                    H  H         H    COOCH.sub.3  O                             1.225  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                   H  H         H    COOCH.sub. 3 O                             1.226  CH.sub.3                                                                           SCH.sub.3                                                                          H  H         H    COOCH.sub.3  O                             1.227  CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                  H  H         H    COOCH.sub.3  O                             1.228  CH.sub.3                                                                           H    H  CH.sub.2 OCH.sub.3                                                                      H    COOCH.sub.3  O                             1.229  CH.sub.3                                                                           H    H  OC.sub.3 H.sub.7i                                                                       H    COOCH.sub.3  O                             1.230  CH.sub.3                                                                           H    H  C.sub.3 H.sub.5cycl.                                                                    H    COOCH.sub.3  O                             1.231  CH.sub.3                                                                           H    H  Cl        H    OC.sub.3 H.sub.7                                                                           O                             1.232  CH.sub.3                                                                           H    H  OCH.sub.3 H    OC.sub.3 H.sub.7                                                                           O                             1.233  CH.sub.3                                                                           H    H  OC.sub.2 H.sub.5                                                                        H    OC.sub.3 H.sub.7                                                                           O                             __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR28##                                                                                                      Melting                                     Compound                          point                                       No.   R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                         R.sup.4   R.sup.7                                                                         R.sup.8                                                                             X [°C.]                                __________________________________________________________________________    2.01  CH.sub.3                                                                         H  H Cl        H  COOCH.sub.3                                                                        O                                             2.02  CH.sub.3                                                                         H  H Br        H  COOCH.sub.3                                                                        O                                             2.03  CH.sub.3                                                                         H  H H         H  COOCH.sub.3                                                                        O                                             2.04  CH.sub.3                                                                         H  H CH.sub.3  H  COOCH.sub.3                                                                        O                                             2.05  CH.sub.3                                                                         H  H OCH.sub.3 H  COOCH.sub.3                                                                        O                                             2.06  CH.sub. 3                                                                        H  H N(CH.sub.3).sub.2                                                                       H  COOCH.sub.3                                                                        O                                             2.07  CH.sub.3                                                                         H  H SCH.sub.3 H  COOCH.sub.3                                                                        O                                             2.08  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H  COOCH.sub.3                                                                        O                                             2.09  CH.sub.3                                                                         H  H OCH.sub.2CF.sub.3                                                                       H  COOCH.sub.3                                                                        O                                             2.10  CH.sub.3                                                                         H  H CF.sub.3  H  COOCH.sub.3                                                                        O                                             2.11  CH.sub.3                                                                         CH.sub.3                                                                         H CH.sub.3  H  COOCH.sub.3                                                                        O                                             2.12  CH.sub.3                                                                         CH.sub.3                                                                         H H         H  COOCH.sub.3                                                                        O                                             2.13  CH.sub.3                                                                         CH.sub.3                                                                         H Cl        H  COOCH.sub.3                                                                        O                                             2.14  CH.sub.3                                                                         CH.sub.3                                                                         H OCH.sub.3 H  COOCH.sub.3                                                                        O                                             2.15  C.sub.2 H.sub.5                                                                  H  H Cl        H  COOCH.sub.3                                                                        O                                             2.16  C.sub.2 H.sub.5                                                                  H  H Br        H  COOCH.sub.3                                                                        O                                             2.17  C.sub.2 H.sub.5                                                                  H  H H         H  COOCH.sub.3                                                                        O                                             2.18  C.sub.2 H.sub.5                                                                  H  H CH.sub.3  H  COOCH.sub.3                                                                        O                                             2.19  C.sub.2 H.sub.5                                                                  H  H OCH.sub.3 H  COOCH.sub.3                                                                        O                                             2.20  C.sub.2 H.sub.5                                                                  H  H N(CH.sub.3).sub.2                                                                       H  COOCH.sub.3                                                                        O                                             2.21  C.sub.2 H.sub.5                                                                  H  H SCH.sub.3 H  COOCH.sub.3                                                                        O                                             2.22  C.sub.2 H.sub. 5                                                                 H  H OC.sub.2 H.sub.5                                                                        H  COOCH.sub.3                                                                        O                                             2.23  C.sub.2 H.sub.5                                                                  H  H OCH.sub.2CF.sub.3                                                                       H  COOCH.sub.3                                                                        O                                             2.24  C.sub.2 H.sub.5                                                                  H  H CF.sub.3  H  COOCH.sub.3                                                                        O                                             2.25  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H CH.sub.3  H  COOCH.sub.3                                                                        O                                             2.26  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H H         H  COOCH.sub.3                                                                        O                                             2.27  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H Cl        H  COOCH.sub.3                                                                        O                                             2.28  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H OCH.sub.3 H  COOCH.sub.3                                                                        O                                             2.29  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H  H    O                                             2.30  CH.sub.3                                                                         H  H Cl        H  H    O                                             2.31  CH.sub.3                                                                         H  H OCH.sub.3 H  H    O                                             2.32  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H  Cl   O                                             2.33  CH.sub.3                                                                         H  H Cl        H  Cl   O                                             2.34  CH.sub.3                                                                         H  H OCH.sub.3 H  Cl   O                                             __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR29##                                                                                                      Melting                                     Compound                          point                                       No.   R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                         R.sup.4   R.sup.7                                                                         R.sup.8                                                                             X [°C.]                                __________________________________________________________________________    3.01  CH.sub.3                                                                         H  H Cl        H COOCH.sub.3                                                                         O                                             3.02  CH.sub.3                                                                         H  H Br        H COOCH.sub.3                                                                         O                                             3.03  CH.sub.3                                                                         H  H H         H COOCH.sub.3                                                                         O                                             3.04  CH.sub.3                                                                         H  H CH.sub.3  H COOCH.sub.3                                                                         O                                             3.05  CH.sub.3                                                                         H  H OCH.sub.3 H COOCH.sub.3                                                                         O                                             3.06  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H COOCH.sub.3                                                                         O                                             3.07  CH.sub.3                                                                         H  H SCH.sub.3 H COOCH.sub.3                                                                         O                                             3.08  CH.sub.3                                                                         H  H N(CH.sub.3).sub.2                                                                       H COOCH.sub.3                                                                         O                                             3.09  CH.sub.3                                                                         H  H OCH.sub.2CF.sub.3                                                                       H COOCH.sub.3                                                                         O                                             3.10  CH.sub.3                                                                         H  H CF.sub.3  H COOCH.sub.3                                                                         O                                             3.11  CH.sub.3                                                                         CH.sub.3                                                                         H CH.sub.3  H COOCH.sub.3                                                                         O                                             3.12  CH.sub.3                                                                         CH.sub.3                                                                         H H         H COOCH.sub.3                                                                         O                                             3.13  CH.sub.3                                                                         CH.sub.3                                                                         H Cl        H COOCH.sub.3                                                                         O                                             3.14  CH.sub.3                                                                         CH.sub.3                                                                         H OCH.sub.3 H COOCH.sub.3                                         3.15  C.sub.2 H.sub.5                                                                  H  H Cl        H COOCH.sub.3                                                                         O                                             3.16  C.sub.2 H.sub.5                                                                  H  H Br        H COOCH.sub.3                                                                         O                                             3.17  C.sub.2 H.sub.5                                                                  H  H H         H COOCH.sub.3                                                                         O                                             3.18  C.sub.2 H.sub.5                                                                  H  H CH.sub.3  H COOCH.sub.3                                                                         O                                             3.19  C.sub.2 H.sub.5                                                                  H  H OCH.sub.3 H COOCH.sub.3                                                                         O                                             3.20  C.sub.2 H.sub.5                                                                  H  H N(CH.sub.3).sub.2                                                                       H COOCH.sub.3                                                                         O                                             3.21  C.sub.2 H.sub.5                                                                  H  H SCH.sub.3 H COOCH.sub.3                                                                         O                                             3.22  C.sub.2 H.sub.5                                                                  H  H OC.sub.2 H.sub.5                                                                        H COOCH.sub.3                                                                         O                                             3.23  C.sub.2 H.sub.5                                                                  H  H OCH.sub.2CF.sub.3                                                                       H COOCH.sub.3                                                                         O                                             3.24  C.sub.2 H.sub.5                                                                  H  H CF.sub.3  H COOCH.sub.3                                                                         O                                             3.25  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H CH.sub.3  H COOCH.sub.3                                                                         O                                             3.26  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H H         H COOCH.sub.3                                                                         O                                             3.27  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H Cl        H COOCH.sub.3                                                                         O                                             3.28  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H OCH.sub.3 H COOCH.sub.3                                                                         O                                             3.29  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H H     O                                             3.30  CH.sub.3                                                                         H  H Cl        H H     O                                             3.31  CH.sub.3                                                                         H  H OCH.sub.3 H H     O                                             3.32  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H Cl    O                                             3.33  CH.sub.3                                                                         H  H Cl        H Cl    O                                             3.34  CH.sub.3                                                                         H  H OCH.sub.3 H Cl    O                                             __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________     ##STR30##                                                                                                      Melting                                     Compound                          point                                       No.   R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                         R.sup.4   R.sup.7                                                                         R.sup.8                                                                             X [°C.]                                __________________________________________________________________________    4.01  CH.sub.3                                                                         H  H Cl        H COOCH.sub.3                                                                         O 206-207                                     4.02  CH.sub.3                                                                         H  H Br        H COOCH.sub.3                                                                         O                                             4.03  CH.sub.3                                                                         H  H H         H COOCH.sub.3                                                                         O                                             4.04  CH.sub.3                                                                         H  H CH.sub.3  H COOCH.sub.3                                                                         O                                             4.05  CH.sub.3                                                                         H  H OCH.sub.3 H COOCH.sub.3                                                                         O                                             4.06  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H COOCH.sub.3                                                                         O                                             4.07  CH.sub.3                                                                         H  H SCH.sub.3 H COOCH.sub.3                                                                         O                                             4.08  CH.sub.3                                                                         H  H N(CH.sub.3).sub.2                                                                       H COOCH.sub.3                                                                         O                                             4.09  CH.sub.3                                                                         H  H OCH.sub.2CF.sub.3                                                                       H COOCH.sub.3                                                                         O                                             4.10  CH.sub.3                                                                         H  H CF.sub.3  H COOCH.sub.3                                                                         O                                             4.11  CH.sub.3                                                                         CH.sub.3                                                                         H CH.sub.3  H COOCH.sub.3                                                                         O                                             4.12  CH.sub.3                                                                         CH.sub.3                                                                         H H         H COOCH.sub.3                                                                         O                                             4.13  CH.sub.3                                                                         CH.sub.3                                                                         H Cl        H COOCH.sub.3                                                                         O                                             4.14  CH.sub.3                                                                         CH.sub.3                                                                         H OCH.sub.3 H COOCH.sub.3                                                                         O                                             4.15  C.sub.2 H.sub.5                                                                  H  H Cl        H COOCH.sub.3                                                                         O                                             4.16  C.sub.2 H.sub.5                                                                  H  H Br        H COOCH.sub.3                                                                         O                                             4.17  C.sub.2 H.sub.5                                                                  H  H H         H COOCH.sub.3                                                                         O                                             4.18  C.sub.2 H.sub.5                                                                  H  H CH.sub.3  H COOCH.sub.3                                                                         O                                             4.19  C.sub.2 H.sub.5                                                                  H  H OCH.sub.3 H COOCH.sub.3                                                                         O                                             4.20  C.sub.2 H.sub.5                                                                  H  H N(CH.sub.3).sub.2                                                                       H COOCH.sub.3                                                                         O                                             4.21  C.sub.2 H.sub.5                                                                  H  H SCH.sub.3 H COOCH.sub.3                                                                         O                                             4.22  C.sub.2 H.sub.5                                                                  H  H OC.sub.2 H.sub.5                                                                        H COOCH.sub.3                                                                         O                                             4.23  C.sub.2 H.sub.5                                                                  H  H OCH.sub.2CF.sub.3                                                                       H COOCH.sub.3                                                                         O                                             4.24  C.sub.2 H.sub.5                                                                  H  H CF.sub.3  H COOCH.sub.3                                                                         O                                             4.25  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H CH.sub.3  H COOCH.sub.3                                                                         O                                             4.26  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H H         H COOCH.sub.3                                                                         O                                             4.27  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H Cl        H COOCH.sub.3                                                                         O                                             4.28  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H OCH.sub.3 H COOCH.sub.3                                                                         O                                             4.29  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H H     O                                             4.30  CH.sub.3                                                                         H  H Cl        H H     O                                             4.31  CH.sub.3                                                                         H  H OCH.sub.3 H H     O                                             4.32  CH.sub.3                                                                         H  H OC.sub.2 H.sub.5                                                                        H Cl    O                                             4.33  CH.sub.3                                                                         H  H Cl        H Cl    O                                             4.34  CH.sub.3                                                                         H  H OCH.sub.3 H Cl    O                                             __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________     ##STR31##                                                                                                      Melting                                     Compound                          point                                       No.   R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                          R.sup.4  R.sup.7                                                                         R.sup.8                                                                             X [°C.]                                __________________________________________________________________________    5.01  CH.sub.3                                                                         H  H  Cl       H Cl    O 202-203 (decomposition)                     5.02  CH.sub.3                                                                         H  H  Br       H Cl    O                                             5.03  CH.sub.3                                                                         H  H  H        H Cl    O                                             5.04  CH.sub.3                                                                         H  H  CH.sub.3 H Cl    O                                             5.05  CH.sub.3                                                                         H  H  OCH.sub.3                                                                              H Cl    O                                             5.06  CH.sub. 3                                                                        H  H  OC.sub.2 H.sub.5                                                                       H Cl    O                                             5.07  CH.sub.3                                                                         H  H  SCH.sub.3                                                                              H Cl    O                                             5.08  CH.sub.3                                                                         H  H  N(CH.sub.3).sub.2                                                                      H Cl    O                                             5.09  CH.sub.3                                                                         H  H  OCH.sub.2CF.sub.3                                                                      H Cl    O                                             5.10  CH.sub.3                                                                         H  H  CF.sub.3 H Cl    O                                             5.11  CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3 H Cl    O                                             5.12  CH.sub.3                                                                         CH.sub.3                                                                         H  H        H Cl    O                                             5.13  CH.sub.3                                                                         CH.sub.3                                                                         H  Cl       H Cl    O                                             5.14  CH.sub.3                                                                         CH.sub.3                                                                         H  OCH.sub.3                                                                              H Cl    O                                             5.15  C.sub.2 H.sub.5                                                                  H  H  Cl       H Cl    O                                             5.16  C.sub.2 H.sub.5                                                                  H  H  Br       H Cl    O                                             5.17  C.sub.2 H.sub.5                                                                  H  H  H        H Cl    O                                             5.18  C.sub.2 H.sub.5                                                                  H  H  CH.sub.3 H Cl    O                                             5.19  C.sub.2 H.sub.5                                                                  H  H  OCH.sub.3                                                                              H Cl    O                                             5.20  C.sub.2 H.sub.5                                                                  H  H  N(CH.sub.3).sub.2                                                                      H Cl    O                                             5.21  C.sub.2 H.sub.5                                                                  H  H  SCH.sub.3                                                                              H Cl    O                                             5.22  C.sub.2 H.sub.5                                                                  H  H  OC.sub.2 H.sub.5                                                                       H Cl    O                                             5.23  C.sub.2 H.sub.5                                                                  H  H  OCH.sub.2CF.sub.3                                                                      H Cl    O                                             5.24  C.sub.2 H.sub.5                                                                  H  H  CF.sub.3 H Cl    O                                             5.25  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  CH.sub.3 H Cl    O                                             5.26  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  H        H Cl    O                                             5.27  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  Cl       H Cl    O                                             5.28  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  OCH.sub.3                                                                              H Cl    O                                             5.29  CH.sub.3                                                                         H  H  OC.sub.2 H.sub.5                                                                       H COOCH.sub.3                                                                         O                                             5.30  CH.sub.3                                                                         H  H  Cl       H COOCH.sub.3                                                                         O                                             5.31  CH.sub.3                                                                         H  H  OCH.sub.3                                                                              H COOCH.sub.3                                                                         O                                             5.32  CH.sub.3                                                                         H  H  OC.sub.2 H.sub.5                                                                       H OCH.sub.3                                                                           O                                             5.33  CH.sub.3                                                                         H  H  Cl       H OCH.sub.3                                                                           O                                             5.34  CH.sub.3                                                                         H  H  OCH.sub.3                                                                              H OCH.sub.3                                                                           O                                             __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR32##                                                                                                      Melting                                     Compound                          point                                       No.   R.sup.1                                                                          R.sup.2                                                                          R.sup.3                                                                          R.sub.4  R.sup.7                                                                         R.sup.8                                                                             X [°C.]                                __________________________________________________________________________    6.01  CH.sub.3                                                                         H  H  Cl       H Cl    O                                             6.02  CH.sub.3                                                                         H  H  Br       H Cl    O                                             6.03  CH.sub.3                                                                         H  H  H        H Cl    O                                             6.04  CH.sub.3                                                                         H  H  CH.sub.3 H Cl    O                                             6.05  CH.sub.3                                                                         H  H  OCH.sub.3                                                                              H Cl    O                                             6.06  CH.sub.3                                                                         H  H  OC.sub. 2 H.sub.5                                                                      H Cl    O                                             6.07  CH.sub.3                                                                         H  H  SCH.sub.3                                                                              H Cl    O                                             6.08  CH.sub.3                                                                         H  H  N(CH.sub.3).sub.2                                                                      H Cl    O                                             6.09  CH.sub.3                                                                         H  H  OCH.sub.2CF.sub.3                                                                      H Cl    O                                             6.10  CH.sub.3                                                                         H  H  CF.sub.3 H Cl    O                                             6.11  CH.sub.3                                                                         CH.sub.3                                                                         H  CH.sub.3 H Cl    O                                             6.12  CH.sub.3                                                                         CH.sub.3                                                                         H  H        H Cl    O                                             6.13  CH.sub.3                                                                         CH.sub.3                                                                         H  Cl       H Cl    O                                             6.14  CH.sub.3                                                                         CH.sub.3                                                                         H  OCH.sub.3                                                                              H Cl    O                                             6.15  C.sub.2 H.sub.5                                                                  H  H  Cl       H Cl    O                                             6.16  C.sub.2 H.sub.5                                                                  H  H  Br       H Cl    O                                             6.17  C.sub.2 H.sub.5                                                                  H  H  H        H Cl    O                                             6.18  C.sub.2 H.sub.5                                                                  H  H  CH.sub.3 H Cl    O                                             6.19  C.sub.2 H.sub.5                                                                  H  H  OCH.sub.3                                                                              H Cl    O                                             6.20  C.sub.2 H.sub.5                                                                  H  H  N(CH.sub.3).sub.2                                                                      H Cl    O                                             6.21  C.sub.2 H.sub.5                                                                  H  H  SCH.sub.3                                                                              H Cl    O                                             6.22  C.sub.2 H.sub.5                                                                  H  H  OC.sub.2 H.sub.5                                                                       H Cl    O                                             6.23  C.sub.2 H.sub.5                                                                  H  H  OCH.sub.2 CF.sub.3                                                                     H Cl    O                                             6.24  C.sub.2 H.sub.5                                                                  H  H  CF.sub.3 H Cl    O                                             6.25  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  CH.sub.3 H Cl    O                                             6.26  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  H        H Cl    O                                             6.27  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  Cl       H Cl    O                                             6.28  C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         H  OCH.sub.3                                                                              H Cl    O                                             6.29  CH.sub.3                                                                         H  H  OC.sub.2 H.sub.5                                                                       H COOCH.sub.3                                                                         O                                             6.30  CH.sub.3                                                                         H  H  Cl       H COOCH.sub.3                                                                         O                                             6.31  CH.sub.3                                                                         H  H  OCH.sub.3                                                                              H COOCH.sub.3                                                                         O                                             6.32  CH.sub.3                                                                         H  H  OC.sub.2 H.sub.5                                                                       H OCH.sub.3                                                                           O                                             6.33  CH.sub.3                                                                         H  H  Cl       H OCH.sub.3                                                                           O                                             6.33  CH.sub.3                                                                         H  H  OCH.sub.3                                                                              H OCH.sub.3                                                                           O                                             __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________     ##STR33##                                                                                                               Melting                            Compound                                   point                              No.   R.sup.1                                                                            R.sup.2    R.sup.3                                                                          R.sup.7                                                                            R.sup.8    X [°C.]                       __________________________________________________________________________    7.01  CH.sub.3                                                                           Cl         H  H    COOCH.sub.3                                                                              O                                    7.02  CH.sub.3                                                                           H          H  H    COOCH.sub.3                                                                              O                                    7.03  CH.sub.3                                                                           CH.sub.3   H  H    COOCH.sub.3                                                                              O 164-165 (decomposition)            7.04  CH.sub.3                                                                           OCH.sub.3  H  H    COOCH.sub.3                                                                              O 181-182 (decomposition)            7.05  CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                        H  H    COOCH.sub.3                                                                              O                                    7.06  CH.sub.3                                                                           SCH.sub.3  H  H    COOCH.sub.3                                                                              O 186-187                            7.07  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    COOCH.sub.3                                                                              O 188 (decomposition)                7.08  CH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                        H  H    COOCH.sub.3                                                                              O                                    7.09  CH.sub.3                                                                           CF.sub.3   H  H    COOCH.sub.3                                                                              O                                    7.10  C.sub.2 H.sub.5                                                                    Cl         H  H    COOCH.sub.3                                                                              O                                    7.11  C.sub.2 H.sub.5                                                                    H          H  H    COOCH.sub.3                                                                              O                                    7.12  C.sub.2 H.sub.5                                                                    CH.sub.3   H  H    COOCH.sub.3                                                                              O                                    7.13  C.sub.2 H.sub.5                                                                    OCH.sub.3  H  H    COOCH.sub.3                                                                              O                                    7.14  C.sub.2 H.sub.5                                                                    N(CH.sub.3).sub.2                                                                        H  H    COOCH.sub.3                                                                              O                                    7.15  C.sub.2 H.sub.5                                                                    SCH.sub.3  H  H    COOCH.sub.3                                                                              O                                    7.16  C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                         H  H    COOCH.sub.3                                                                              O                                    7.17  C.sub.2 H.sub.5                                                                    OCH.sub.2CF.sub.3                                                                        H  H    COOCH.sub.3                                                                              O                                    7.18  C.sub.2 H.sub.5                                                                    CF.sub.3   H  H    COOCH.sub.3                                                                              O                                    7.19  CH.sub.3                                                                           OCH.sub.2CH.sub.2 OCH.sub.3                                                              H  H    COOCH.sub.3                                                                              O 136 (decomposition)                7.20  CH.sub.3                                                                           Cl         H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.21  CH.sub.3                                                                           H          H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.22  CH.sub.3                                                                           CH.sub.3   H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.23  CH.sub.3                                                                           OCH.sub.3  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.24  CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                        H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.25  CH.sub.3                                                                           SCH.sub.3  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.26  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.27  CH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                        H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.28  CH.sub.3                                                                           CF.sub.3   H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.29  C.sub.2 H.sub.5                                                                    Cl         H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.30  C.sub.2 H.sub.5                                                                    H          H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.31  C.sub.2 H.sub.5                                                                    CH.sub.3   H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.32  C.sub.2 H.sub.5                                                                    OCH.sub.3  H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.33  C.sub.2 H.sub.5                                                                    N(CH.sub.3).sub.2                                                                        H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.34  C.sub.2 H.sub.5                                                                    SCH.sub. 3 H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.35  C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                         H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.36  C.sub.2 H.sub.5                                                                    OCH.sub.2CF.sub.3                                                                        H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.37  C.sub.2 H.sub.5                                                                    CF.sub.3   H  H    SO.sub.2 N(CH.sub.3).sub.2                                                               O                                    7.38  CH.sub.3                                                                           Cl         H  H    OC.sub.2 H.sub.5                                                                         O                                    7.39  CH.sub.3                                                                           H          H  H    OC.sub.2 H.sub.5                                                                         O                                    7.40  CH.sub.3                                                                           CH.sub.3   H  H    OC.sub.2 H.sub.5                                                                         O                                    7.41  CH.sub.3                                                                           OCH.sub.3  H  H    OC.sub.2 H.sub.5                                                                         O                                    7.42  CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                        H  H    OC.sub.2 H.sub.5                                                                         O                                    7.43  CH.sub.3                                                                           SCH.sub.3  H  H    OC.sub.2 H.sub.5                                                                         O                                    7.44  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OC.sub.2 H.sub.5                                                                         O                                    7.45  CH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                        H  H    OC.sub.2 H.sub.5                                                                         O                                    7.46  CH.sub.3                                                                           CF.sub.3   H  H    OC.sub.2 H.sub.5                                                                         O                                    7.47  C.sub.2 H.sub.5                                                                    Cl         H  H    OC.sub.2 H.sub.5                                                                         O                                    7.48  C.sub.2 H.sub.5                                                                    H          H  H    OC.sub.2 H.sub.5                                                                         O                                    7.49  C.sub.2 H.sub.5                                                                    CH.sub.3   H  H    OC.sub.2 H.sub.5                                                                         O                                    7.50  C.sub.2 H.sub.5                                                                    OCH.sub.3  H  H    OC.sub.2 H.sub.5                                                                         O                                    7.51  C.sub.2 H.sub.5                                                                    N(CH.sub.3).sub.2                                                                        H  H    OC.sub.2 H.sub.5                                                                         O                                    7.52  C.sub.2 H.sub.5                                                                    SCH.sub.3  H  H    OC.sub.2 H.sub.5                                                                         O                                    7.53  C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                         H  H    OC.sub.2 H.sub.5                                                                         O                                    7.54  C.sub.2 H.sub.5                                                                    OCH.sub.2CF.sub.3                                                                        H  H    OC.sub.2 H.sub.5                                                                         O                                    7.55  C.sub.2 H.sub.5                                                                    CF.sub.3   H  H    OC.sub.2 H.sub.5                                                                         O                                    7.56  CH.sub.3                                                                           Cl         H  H    OCHF.sub.2 O                                    7.57  CH.sub.3                                                                           H          H  H    OCHF.sub.2 O                                    7.58  CH.sub.3                                                                           CH.sub.3   H  H    OCHF.sub.2 O 157-158                            7.59  CH.sub.3                                                                           OCH.sub.3  H  H    OCHF.sub.2 O 159-161                            7.60  CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                        H  H    OCHF.sub.2 O                                    7.61  CH.sub.3                                                                           SCH.sub.3  H  H    OCHF.sub.2 O                                    7.62  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCHF.sub.2 O                                    7.63  CH.sub.3                                                                           OCH.sub.2CF.sub.3                                                                        H  H    OCHF.sub.2 O                                    7.64  CH.sub.3                                                                           CF.sub.3   H  H    OCHF.sub.2 O                                    7.65  C.sub.2 H.sub.5                                                                    Cl         H  H    OCHF.sub.2 O                                    7.66  C.sub.2 H.sub.5                                                                    H          H  H    OCHF.sub.2 O                                    7.67  C.sub.2 H.sub.5                                                                    CH.sub.3   H  H    OCHF.sub.2 O                                    7.68  C.sub.2 H.sub.5                                                                    OCH.sub.3  H  H    OCHF.sub.2 O                                    7.69  C.sub.2 H.sub.5                                                                    N(CH.sub.3).sub.2                                                                        H  H    OCHF.sub.2 O                                    7.70  C.sub.2 H.sub.5                                                                    SCH.sub.3  H  H    OCHF.sub.2 O                                    7.71  C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                         H  H    OCHF.sub.2 O                                    7.72  C.sub.2 H.sub.5                                                                    OCH.sub.2CF.sub.3                                                                        H  H    OCHF.sub.2 O                                    7.73  C.sub.2 H.sub.5                                                                    CF.sub.3   H  H    OCHF.sub.2 O                                    7.74  CH.sub.3                                                                           Cl         H  H    CF.sub.3   O                                    7.75  CH.sub.3                                                                           H          H  H    CF.sub.3   O                                    7.76  CH.sub.3                                                                           CH.sub.3   H  H    CF.sub.3   O                                    7.77  CH.sub.3                                                                           OCH.sub.3  H  H    CF.sub.3   O                                    7.78  CH.sub.3                                                                           N(CH.sub.3).sub.2                                                                        H  H    CF.sub.3   O                                    7.79  CH.sub.3                                                                           SCH.sub.3  H  H    CF.sub.3   O                                    7.80  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    CF.sub.3   O                                    7.81  CH.sub.3                                                                           OCH.sub. 2CF.sub.3                                                                       H  H    CF.sub.3   O                                    7.82  CH.sub.3                                                                           CF.sub.3   H  H    CF.sub.3   O                                    7.83  C.sub.2 H.sub.5                                                                    Cl         H  H    CF.sub.3   O                                    7.84  C.sub.2 H.sub.5                                                                    H          H  H    CF.sub.3   O                                    7.85  C.sub.2 H.sub.5                                                                    CH.sub.3   H  H    CF.sub.3   O                                    7.86  C.sub.2 H.sub.5                                                                    OCH.sub.3  H  H    CF.sub.3   O                                    7.87  C.sub.2 H.sub.5                                                                    N(CH.sub.3).sub.2                                                                        H  H    CF.sub.3   O                                    7.88  C.sub.2 H.sub.5                                                                    SCH.sub.3  H  H    CF.sub.3   O                                    7.89  C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                         H  H    CF.sub.3   O                                    7.90  C.sub.2 H.sub.5                                                                    OCH.sub.2CF.sub.3                                                                        H  H    CF.sub.3   O                                    7.91  C.sub.2 H.sub.5                                                                    CF.sub.3   H  H    CF.sub.3   O                                    7.92  C.sub.3 H.sub.7i                                                                   OC.sub.2 H.sub.5                                                                         H  H    COOCH.sub.3                                                                              O                                    7.93  C.sub.3 H.sub.7i                                                                   CH.sub.3   H  H    COOCH.sub.3                                                                              O                                    7.94  C.sub.3 H.sub.7i                                                                   OCH.sub.3  H  H    COOCH.sub.3                                                                              O                                    7.95  CH.sub.3                                                                           CH.sub.3   H  H    COOCH.sub.3                                                                              S                                    7.96  CH.sub.3                                                                           CH.sub.3   CH.sub.3                                                                         H    COOCH.sub.3                                                                              O                                    7.97  CH.sub.3                                                                           CH.sub.3   C.sub.2 H.sub.5                                                                  H    COOCH.sub.3                                                                              O                                    7.98  CH.sub.3                                                                           CH.sub.3   H  5-OCH.sub.3                                                                        COOCH.sub.3                                                                              O                                    7.99  CH.sub.3                                                                           CH.sub.3   H  5-F  COOCH.sub.3                                                                              O                                    7.100 CH.sub.3                                                                           CH.sub.3   H  6-Cl COOCH.sub.3                                                                              O                                    7.101 C.sub.3 H.sub.7i                                                                   OC.sub.2 H.sub.5                                                                         H  H    OCHF.sub.2 O                                    7.102 C.sub.3 H.sub.7i                                                                   CH.sub.3   H  H    OCHF.sub.2 O                                    7.103 C.sub.3 H.sub.7i                                                                   OCH.sub.3  H  H    OCHF.sub.2 O                                    7.104 CH.sub.3                                                                           CH.sub.3   H  H    OCHF.sub.2 S                                    7.105 CH.sub.3                                                                           CH.sub.3   CH.sub.3                                                                         H    OCHF.sub.2 O                                    7.106 CH.sub.3                                                                           CH.sub.3   C.sub.2 H.sub.5                                                                  H    OCHF.sub.2 O                                    7.107 CH.sub.3                                                                           CH.sub.3   H  5-OCH.sub.3                                                                        OCHF.sub.2 O                                    7.108 CH.sub.3                                                                           CH.sub.3   H  5-F  OCHF.sub.2 O                                    7.109 CH.sub.3                                                                           CH.sub.3   H  6-Cl OCHF.sub.2 O                                    7.110 CH.sub.3                                                                           OCH.sub.3  H  H    CHF.sub.2  O                                    7.111 CH.sub.3                                                                           CH.sub.3   H  H    CHF.sub.2  O                                    7.112 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    CHF.sub.2  O                                    7.113 CH.sub.3                                                                           OCH.sub.3  H  H    OCH.sub.3  O                                    7.114 CH.sub.3                                                                           CH.sub.3   H  H    OCH.sub.3  O                                    7.115 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCH.sub.3  O                                    7.116 CH.sub.3                                                                           OCH.sub.3  H  H    OCH.sub.2CH.sub.2 Cl                                                                     O                                    7.117 CH.sub.3                                                                           CH.sub.3   H  H    OCH.sub.2CH.sub.2 Cl                                                                     O                                    7.118 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCH.sub.2CH.sub.2 Cl                                                                     O                                    7.119 CH.sub.3                                                                           OCH.sub.3  H  H    OCH.sub.2CH.sub.2 OCH.sub.3                                                              O                                    7.120 CH.sub.3                                                                           CH.sub.3   H  H    OCH.sub.2CH.sub.2 OCH.sub.3                                                              O                                    7.121 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCH.sub.2CH.sub.2 OCH.sub.3                                                              O                                    7.122 CH.sub.3                                                                           OCH.sub.3  H  H    OCH.sub.2CF.sub.3                                                                        O                                    7.123 CH.sub.3                                                                           CH.sub.3   H  H    OCH.sub.2CF.sub.3                                                                        O                                    7.124 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCH.sub.2CF.sub.3                                                                        O                                    7.125 CH.sub.3                                                                           OCH.sub.3  H  H    OCClCHCl   O                                    7.126 CH.sub.3                                                                           CH.sub.3   H  H    OCClCHCl   O                                    7.127 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCClCHCl   O                                    7.128 CH.sub.3                                                                           OCH.sub.3  H  H    NO.sub.2   O                                    7.129 CH.sub.3                                                                           CH.sub.3   H  H    NO.sub.2   O                                    7.130 CH.sub.3                                                                           OC.sub.2 H.sub. 5                                                                        H  H    NO.sub.2   O                                    7.131 CH.sub.3                                                                           OCH.sub.3  H  H    COOC.sub.2 H.sub.5                                                                       O                                    7.132 CH.sub.3                                                                           CH.sub.3   H  H    COOC.sub.2 H.sub.5                                                                       O                                    7.133 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    COOC.sub.2 H.sub.5                                                                       O                                    7.134 CH.sub.3                                                                           OCH.sub.3  H  H    Cl         O                                    7.135 CH.sub.3                                                                           CH.sub.3   H  H    Cl         O 178-179                            7.136 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    Cl         O                                    7.137 CH.sub.3                                                                           OCH.sub.3  H  H    F          O                                    7.138 CH.sub.3                                                                           CH.sub.3   H  H    F          O                                    7.139 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    F          O                                    7.140 CH.sub.3                                                                           OCH.sub.3  H  H    Br         O                                    7.141 CH.sub.3                                                                           CH.sub.3   H  H    Br         O                                    7.142 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    Br         O                                    7.143 CH.sub.3                                                                           OCH.sub.3  H  H    CH.sub.3   O                                    7.144 CH.sub.3                                                                           CH.sub.3   H  H    CH.sub.3   O                                    7.145 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    CH.sub.3   O                                    7.146 CH.sub.3                                                                           OCH.sub.3  H  H    SCH.sub.3  O                                    7.147 CH.sub.3                                                                           CH.sub.3   H  H    SCH.sub.3  O                                    7.148 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    SCH.sub.3  O                                    7.149 CH.sub.3                                                                           OCH.sub.3  H  H    SCHF.sub.2 O                                    7.150 CH.sub.3                                                                           CH.sub.3   H  H    SCHF.sub.2 O                                    7.151 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    SCHF.sub.2 O                                    7.152 CH.sub.3                                                                           CH.sub.3   H  H    SCH.sub.2CH.sub.2 Cl                                                                     O                                    7.153 CH.sub.3                                                                           OCH.sub.3  H  H    SCH.sub.2CH.sub.2 Cl                                                                     O                                    7.154 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    SCH.sub.2CH.sub.2 Cl                                                                     O                                    7.155 CH.sub.3                                                                           CH.sub.3   H  H    SO.sub.2CH.sub.3                                                                         O                                    7.156 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    SO.sub.2CH.sub.3                                                                         O                                    7.157 CH.sub.3                                                                           OCH.sub.3  H  H    SO.sub.2CH.sub.3                                                                         O                                    7.158 CH.sub.3                                                                           CH.sub.3   H  H    SO.sub.2C.sub.2 H.sub.5                                                                  O                                    7.159 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    SO.sub.2C.sub.2 H.sub.5                                                                  O                                    7.160 CH.sub.3                                                                           OCH.sub.3  H  H    SO.sub.2C.sub.2 H.sub.5                                                                  O                                    7.161 CH.sub.3                                                                           CH.sub.3   H  H    OCH.sub.2CHCH.sub.2                                                                      O                                    7.162 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OCH.sub.2CHCH.sub.2                                                                      O                                    7.163 CH.sub.3                                                                           OCH.sub.3  H  H    OCH.sub. 2CHCH.sub.2                                                                     O                                    7.164 CH.sub.3                                                                           OCH.sub.3  H  H    H          O                                    7.165 CH.sub.3                                                                           CH.sub.3   H  H    H          O                                    7.166 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    H          O                                    7.167 CH.sub.3                                                                           OCH.sub.3  H  H    OSO.sub.2 CH.sub.3                                                                       O                                    7.168 CH.sub.3                                                                           CH.sub.3   H  H    OSO.sub.2 CH.sub.3                                                                       O                                    7.169 CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                         H  H    OSO.sub.2 CH.sub.3                                                                       O                                    __________________________________________________________________________

                  TABLE 8                                                         ______________________________________                                         ##STR34##                                                                                                                 Melt-                            Com-                                         ing                              pound                                        point                            No.   R.sup.1                                                                              R.sup.2     R.sup.3                                                                           R.sup.7                                                                           R.sup.8 X   [°C.]                     ______________________________________                                        8.01  CH.sub.3                                                                             Cl          H   H   COOCH.sub.3                                                                           O                                    8.02  CH.sub.3                                                                             H           H   H   COOCH.sub.3                                                                           O                                    8.03  CH.sub.3                                                                             CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    8.04  CH.sub.3                                                                             OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    8.05  CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                         H   H   COOCH.sub.3                                                                           O                                    8.06  CH.sub. 3                                                                            SCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    8.07  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    8.08  CH.sub.3                                                                             OCH.sub.2CF.sub.3                                                                         H   H   COOCH.sub.3                                                                           O                                    8.09  CH.sub.3                                                                             CF.sub.3    H   H   COOCH.sub.3                                                                           O                                    8.10  C.sub.2 H.sub.5                                                                      Cl          H   H   COOCH.sub.3                                                                           O                                    8.11  C.sub.2 H.sub.5                                                                      H           H   H   COOCH.sub.3                                                                           O                                    8.12  C.sub.2 H.sub.5                                                                      CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    8.13  C.sub.2 H.sub.5                                                                      OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    8.14  C.sub.2 H.sub.5                                                                      N(CH.sub.3).sub.2                                                                         H   H   COOCH.sub.3                                                                           O                                    8.15  C.sub.2 H.sub.5                                                                      SCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    8.16  C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    8.17  C.sub.2 H.sub.5                                                                      OCH.sub.2CF.sub.3                                                                         H   H   COOCH.sub.3                                                                           O                                    8.18  C.sub.2 H.sub.5                                                                      CF.sub.3    H   H   COOCH.sub.3                                                                           O                                    8.19  CH.sub.3                                                                             OCH.sub.3   H   H   H       O                                    8.20  CH.sub.3                                                                             CH.sub.3    H   H   H       O                                    8.21  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   H       O                                    8.22  CH.sub.3                                                                             OCH.sub.3   H   H   Cl      O                                    8.23  CH.sub.3                                                                             CH.sub.3    H   H   Cl      O                                    8.24  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR35##                                                                                                                 Melt-                            Com-                                         ing                              pound                                        point                            No.   R.sup.1                                                                              R.sup.2     R.sup.3                                                                           R.sup.7                                                                           R.sup.8 X   [°C.]                     ______________________________________                                        9.01  CH.sub.3                                                                             Cl          H   H   COOCH.sub.3                                                                           O                                    9.02  CH.sub.3                                                                             H           H   H   COOCH.sub.3                                                                           O                                    9.03  CH.sub.3                                                                             CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    9.04  CH.sub.3                                                                             OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    9.05  CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                         H   H   COOCH.sub.3                                                                           O                                    9.06  CH.sub.3                                                                             SCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    9.07  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    9.08  CH.sub.3                                                                             OCH.sub.2CF.sub.3                                                                         H   H   COOCH.sub.3                                                                           O                                    9.09  CH.sub.3                                                                             CF.sub.3    H   H   COOCH.sub.3                                                                           O                                    9.10  C.sub.2 H.sub.5                                                                      Cl          H   H   COOCH.sub.3                                                                           O                                    9.11  C.sub.2 H.sub.5                                                                      H           H   H   COOCH.sub.3                                                                           O                                    9.12  C.sub.2 H.sub.5                                                                      CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    9.13  C.sub.2 H.sub.5                                                                      OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    9.14  C.sub.2 H.sub.5                                                                      N(CH.sub.3).sub.2                                                                         H   H   COOCH.sub.3                                                                           O                                    9.15  C.sub.2 H.sub.5                                                                      SCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    9.16  C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    9.17  C.sub.2 H.sub.5                                                                      OCH.sub.2CF.sub.3                                                                         H   H   COOCH.sub.3                                                                           O                                    9.18  C.sub.2 H.sub.5                                                                      CF.sub.3    H   H   COOCH.sub.3                                                                           O                                    9.19  CH.sub.3                                                                             OCH.sub.3   H   H   H       O                                    9.20  CH.sub.3                                                                             CH.sub.3    H   H   H       O                                    9.21  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   H       O                                    9.22  CH.sub.3                                                                             OCH.sub.3   H   H   Cl      O                                    9.23  CH.sub.3                                                                             CH.sub.3    H   H   Cl      O                                    9.24  CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR36##                                                                                                                 Melt-                            Com-                                         ing                              pound                                        point                            No.   R.sup.1                                                                              R.sup.2     R.sup.3                                                                           R.sup.7                                                                           R.sup.8 X   [°C.]                     ______________________________________                                        10.01 CH.sub.3                                                                             Cl          H   H   COOCH.sub.3                                                                           O                                    10.02 CH.sub.3                                                                             H           H   H   COOCH.sub.3                                                                           O                                    10.03 CH.sub.3                                                                             CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    10.04 CH.sub.3                                                                             OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    10.05 CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                         H   H   COOCH.sub.3                                                                           O                                    10.06 CH.sub. 3                                                                            SCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    10.07 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    10.08 CH.sub.3                                                                             OCH.sub.2CF.sub.3                                                                         H   H   COOCH.sub.3                                                                           O                                    10.09 CH.sub.3                                                                             CF.sub.3    H   H   COOCH.sub.3                                                                           O                                    10.10 C.sub.2 H.sub.5                                                                      Cl          H   H   COOCH.sub.3                                                                           O                                    10.11 C.sub.2 H.sub.5                                                                      H           H   H   COOCH.sub.3                                                                           O                                    10.12 C.sub.2 H.sub.5                                                                      CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    10.13 C.sub.2 H.sub.5                                                                      OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    10.14 C.sub.2 H.sub.5                                                                      N(CH.sub.3).sub.2                                                                         H   H   COOCH.sub.3                                                                           O                                    10.15 C.sub.2 H.sub.5                                                                      SCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    10.16 C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    10.17 C.sub.2 H.sub.5                                                                      OCH.sub.2CF.sub.3                                                                         H   H   COOCH.sub.3                                                                           O                                    10.18 C.sub.2 H.sub.5                                                                      CF.sub.3    H   H   COOCH.sub.3                                                                           O                                    10.19 CH.sub.3                                                                             OCH.sub.3   H   H   H       O                                    10.20 CH.sub.3                                                                             CH.sub.3    H   H   H       O                                    10.21 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   H       O                                    10.22 CH.sub.3                                                                             OCH.sub.3   H   H   Cl      O                                    10.23 CH.sub.3                                                                             CH.sub.3    H   H   Cl      O                                    10.24 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR37##                                                                                                                 Melt-                            Com-                                         ing                              pound                                        point                            No.   R.sup.1                                                                              R.sup.2     R.sup.3                                                                           R.sup.7                                                                           R.sup.8 X   [°C.]                     ______________________________________                                        11.01 CH.sub.3                                                                             Cl          H   H   Cl      O                                    11.02 CH.sub.3                                                                             H           H   H   Cl      O                                    11.03 CH.sub.3                                                                             CH.sub.3    H   H   Cl      O                                    11.04 CH.sub.3                                                                             OCH.sub.3   H   H   Cl      O                                    11.05 CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                         H   H   Cl      O                                    11.06 CH.sub.3                                                                             SCH.sub.3   H   H   Cl      O                                    11.07 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    11.08 CH.sub.3                                                                             OCH.sub.2CF.sub.3                                                                         H   H   Cl      O                                    11.09 CH.sub.3                                                                             CF.sub.3    H   H   Cl      O                                    11.10 C.sub.2 H.sub.5                                                                      Cl          H   H   Cl      O                                    11.11 C.sub.2 H.sub.5                                                                      H           H   H   Cl      O                                    11.12 C.sub.2 H.sub.5                                                                      CH.sub.3    H   H   Cl      O                                    11.13 C.sub.2 H.sub.5                                                                      OCH.sub.3   H   H   Cl      O                                    11.14 C.sub.2 H.sub.5                                                                      N(CH.sub.3).sub.2                                                                         H   H   Cl      O                                    11.15 C.sub.2 H.sub.5                                                                      SCH.sub.3   H   H   Cl      O                                    11.16 C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    11.17 C.sub.2 H.sub.5                                                                      OCH.sub.2CF.sub.3                                                                         H   H   Cl      O                                    11.18 C.sub.2 H.sub.5                                                                      CF.sub.3    H   H   Cl      O                                    11.19 CH.sub.3                                                                             OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    11.20 CH.sub.3                                                                             CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    11.21 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   COOCH.sub.3                                                                           O                                    11.22 CH.sub.3                                                                             OCH.sub.3   H   H   OCH.sub.3                                                                             O                                    11.23 CH.sub.3                                                                             CH.sub.3    H   H   OCH.sub.3                                                                             O                                    11.24 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   OCH.sub.3                                                                             O                                    ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR38##                                                                                                                 Melt-                            Com-                                         ing                              pound                                        point                            No.   R.sup.1                                                                              R.sup.2     R.sup.3                                                                           R.sup.7                                                                           R.sup.8 X   [°C.]                     ______________________________________                                        12.01 CH.sub.3                                                                             Cl          H   H   Cl      O                                    12.02 CH.sub.3                                                                             H           H   H   Cl      O                                    12.03 CH.sub.3                                                                             CH.sub.3    H   H   Cl      O                                    12.04 CH.sub.3                                                                             OCH.sub.3   H   H   Cl      O                                    12.05 CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                         H   H   Cl      O                                    12.06 CH.sub.3                                                                             SCH.sub.3   H   H   Cl      O                                    12.07 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    12.08 CH.sub.3                                                                             OCH.sub.2CF.sub.3                                                                         H   H   Cl      O                                    12.09 CH.sub.3                                                                             CF.sub.3    H   H   Cl      O                                    12.10 C.sub.2 H.sub.5                                                                      Cl          H   H   Cl      O                                    12.11 C.sub.2 H.sub.5                                                                      H           H   H   Cl      O                                    12.12 C.sub.2 H.sub.5                                                                      CH.sub.3    H   H   Cl      O                                    12.13 C.sub.2 H.sub.5                                                                      OCH.sub.3   H   H   Cl      O                                    12.14 C.sub.2 H.sub.5                                                                      N(CH.sub.3).sub.2                                                                         H   H   Cl      O                                    12.15 C.sub.2 H.sub.5                                                                      SCH.sub.3   H   H   Cl      O                                    12.16 C.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                          H   H   Cl      O                                    12.17 C.sub.2 H.sub.5                                                                      OCH.sub.2CF.sub.3                                                                         H   H   Cl      O                                    12.18 C.sub.2 H.sub.5                                                                      CF.sub.3    H   H   Cl      O                                    12.19 CH.sub.3                                                                             OCH.sub.3   H   H   COOCH.sub.3                                                                           O                                    12.20 CH.sub.3                                                                             CH.sub.3    H   H   COOCH.sub.3                                                                           O                                    12.21 CH.sub.3                                                                             OC.sub.2 H.sub.4                                                                          H   H   COOCH.sub.3                                                                           O                                    12.22 CH.sub.3                                                                             OCH.sub.3   H   H   OCH.sub.3                                                                             O                                    12.23 CH.sub.3                                                                             CH.sub.3    H   H   OCH.sub.3                                                                             O                                    12.24 CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                          H   H   OCH.sub.3                                                                             O                                    ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR39##                                                                    Com-                               Melting                                    pound                              point                                      No.   R.sup.1  R.sup.2        R.sup.3                                                                            [°C.]                               ______________________________________                                        13.01 CH.sub.3 Cl             H                                               13.02 CH.sub.3 H              H                                               13.03 CH.sub.3 OCH.sub.3      H    198-199                                    13.05 CH.sub.3 N(CH.sub.3).sub.2                                                                            H                                               13.07 CH.sub.3 OC.sub.2 H.sub.5                                                                             H    167-168                                    13.08 CH.sub.3 OCH.sub.2CF.sub.3                                                                            H                                               13.09 CH.sub.3 CF.sub.3       H                                               13.06 CH.sub.3 SCH.sub.3      H    234                                        13.12 CH.sub.3 CH.sub.3       H    205                                        13.10 C.sub.2 H.sub.5                                                                        Cl             H                                               13.11 C.sub.2 H.sub.5                                                                        H              H                                               13.12 C.sub.2 H.sub.5                                                                        CH.sub.3       H                                               13.13 C.sub.2 H.sub.5                                                                        OCH.sub.3      H                                               13.14 C.sub.2 H.sub.5                                                                        N(CH.sub.3).sub.2                                                                            H                                               13.15 C.sub.2 H.sub.5                                                                        SCH.sub.3      H                                               13.16 C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                             H                                               13.17 C.sub.2 H.sub.5                                                                        OCH.sub.2CF.sub.3                                                                            H                                               13.18 C.sub.2 H.sub.5                                                                        CF.sub.3       H                                               13.19 C.sub.2 H.sub.7i                                                                       OC.sub.2 H.sub.5                                                                             H                                               13.20 C.sub.2 H.sub.7i                                                                       CH.sub.3       H                                               13.21 C.sub.2 H.sub.7i                                                                       OCH.sub.3      H                                               13.22 CH.sub.3 CH.sub.3       CH.sub.3                                        13.23 CH.sub.3 CH.sub.3       C.sub.2 H.sub.5                                 13.24 CH.sub.3 OCH.sub.2CH.sub.2 OCH.sub.3                                                                  H    141-143                                    13.25 CH.sub.3 SOCH.sub.3     H    189                                                                           (decomposition)                            13.26 CH.sub.3 SO.sub.2 CH.sub.3                                                                            H    160                                                                           (decomposition)                            ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                         ##STR40##                                                                    Com-                                    Melting                               pound                                   point                                 No. R.sup.1    R.sup.2  R.sup.3                                                                            R.sup.4    [°C.]                          ______________________________________                                        14.01 CH.sub.3 H        H    Br         251-253                               14.02 CH.sub.3 H        H    CH.sub.3                                         14.03 CH.sub.3 H        H    OCH.sub.3  161-162                               14.04 CH.sub.3 H        H    N(CH.sub.3).sub.2                                14.05 CH.sub.3 H        H    SCH.sub.3                                        14.06 CH.sub.3 H        H    OC.sub.2 H.sub.5                                 14.07 CH.sub.3 H        H    OCH.sub.2CF.sub.3                                14.08 CH.sub.3 H        H    CF.sub.3                                         14.09 CH.sub.3 H        H    H          166-167                               14.10 CH.sub.3 H        H    Cl         265-266                               14.11 CH.sub.3 CH.sub.3 H    CH.sub.3                                         14.12 CH.sub.3 CH.sub.3 H    H          217-219                               14.13 CH.sub.3 CH.sub.3 H    Cl                                               14.14 CH.sub.3 CH.sub.3 H    OCH.sub.3                                        14.15 C.sub.2 H.sub.5                                                                        H        H    Cl                                               14.16 C.sub.2 H.sub.5                                                                        H        H    Br         227-230                               14.17 C.sub.2 H.sub.5                                                                        H        H    H                                                14.18 C.sub.2 H.sub.5                                                                        H        H    CH.sub.3                                         14.19 C.sub.2 H.sub.5                                                                        H        H    OCH.sub.3                                        14.20 C.sub.2 H.sub.5                                                                        H        H    N(CH.sub.3).sub.2                                14.21 C.sub.2 H.sub.5                                                                        H        H    SCH.sub.3                                        14.22 C.sub.2 H.sub.5                                                                        H        H    OC.sub.2 H.sub.5                                 14.23 C.sub.2 H.sub.5                                                                        H        H    OCH.sub.2CF.sub.3                                14.24 C.sub.2 H.sub.5                                                                        H        H    CF.sub.3                                         14.25 C.sub.2 H.sub.5                                                                        CH.sub.3 H    CH.sub.3                                         14.26 C.sub.2 H.sub.5                                                                        CH.sub.3 H    H                                                14.27 C.sub.2 H.sub.5                                                                        CH.sub.3 H    Cl                                               14.28 C.sub.2 H.sub.5                                                                        CH.sub.3 H    OCH.sub.3                                        14.29 C.sub.3 H.sub.7i                                                                       H        H    Cl                                               14.30 C.sub.3 H.sub.7i                                                                       H        H    CH.sub.3                                         14.31 C.sub.3 H.sub.7i                                                                       H        H    OCH.sub.3                                        14.32 CH.sub.3 H        CH.sub.3                                                                           Cl         155-156                               14.33 CH.sub.3 H        C.sub.2 H.sub.5                                                                    Cl                                               14.34 CH.sub.3 OCH.sub.3                                                                              H    H                                                14.35 C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                              H    H                                                14.36 CH.sub.3 OC.sub.2 H.sub.5                                                                       H    H                                                14.37 CH.sub.3 SCH.sub.3                                                                              H    H                                                14.38 CH.sub.3 N(CH.sub.3).sub.2                                                                      H    H                                                14.39 CH.sub.3 OCH.sub.3                                                                              H    Br                                               14.40 CH.sub.3 OCH.sub.3                                                                              H    Cl                                               14.41 CH.sub.3 Br       H    Cl                                               14.42 CH.sub.3 H        H    CH.sub.2OCH.sub.3                                14.43 CH.sub.3 Cl       H    Cl                                               ______________________________________                                    

Formulation examples Example F 1: Formulation examples for activesubstances of the formula I (%=per cent by weight)

    ______________________________________                                        (a) Wettable powder                                                                              (a)      (b)     (c)                                       ______________________________________                                        Active substance No. 7.04                                                                        20%      50%     0.5%                                      Na ligninsulfonate 5%       5%      5%                                        Na laurylsulfate   3%       --      --                                        Na diisobutylnaphthalenesulfonate                                                                --       6%      6%                                        Octylphenolpolyethylene glycol                                                                   --       2%      2%                                        ether/7-8 mol of EO)                                                          Highly disperse silicic acid                                                                     5%       27%     27%                                       Kaolin             67%      --      --                                        Sodium chloride    --       --      59.5%                                     ______________________________________                                    

The active substances is mixed thoroughly with the additives and themixture is ground thoroughly in a suitable mill. Wettable powders whichcan be diluted with water to give suspensions of any desiredconcentration are obtained.

    ______________________________________                                        (b) Emulsion concentrate                                                                            (a)    (b)                                              ______________________________________                                        Active substance No. 1.01                                                                           10%    1%                                               Octylphenolpolyethylene glycol                                                                       3%    3%                                               ether (455 mol of EO)                                                         Ca dodecylbenzenesulfonate                                                                           3%    3%                                               Castor oil polyglycol ether                                                                          4%    4%                                               (36 mol of EO)                                                                Cyclohexanone         30%    10%                                              Xylene mixture        50%    79%                                              ______________________________________                                    

Emulsions of any desired concentration can be prepared from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dust            (a)     (b)                                               ______________________________________                                        Active substance No. 7.07                                                                          0.1%    1%                                               Talc                99.9%   --                                                Kaolin              --      99%                                               ______________________________________                                    

Ready-to-use dusts are obtained by mixing the active substance with thecarrier and grinding the mixture on a suitable mill.

    ______________________________________                                        (d) Extruder granules                                                                             (a)    (b)                                                ______________________________________                                        Active substance No. 1.05                                                                         10%    1%                                                 Na ligninsulfonate   2%    2%                                                 Carboxymethylcellulose                                                                             1%    1%                                                 Kaolin              87%    96%                                                ______________________________________                                    

The active substance is mixed with the additives and the mixture isground and moistened with water. This mixture is extruded and then driedin a stream of air.

    ______________________________________                                        (e) Coated granules                                                           ______________________________________                                        Active substance No. 1.03                                                                          3%                                                       Polyethylene glycol (molecular                                                                     3%                                                       weight 200)                                                                   Kaolin               94%                                                      ______________________________________                                    

The finely ground active substance is uniformly applied to the kaolinmoistened with polyethylene glycol in a mixer. Dust-free coated granulesare obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate                                                                         (a)       (b)                                            ______________________________________                                        Active substance No. 7.07                                                                          40%       5%                                             Ethylene glycol      10%       10%                                            Nonylphenolpolyethylene glycol ether                                                               6%        1%                                             (15 mol of EO)                                                                Na ligninsulfonate   10%       5%                                             Carboxymethylcellulose                                                                             1%        1%                                             37% aqueous formaldehyde solution                                                                  0.2%      0.2%                                           Silicone oil in the form of a                                                                      0.8%      0.8%                                           75% aqueous emulsion                                                          Water                32%       77%                                            ______________________________________                                    

The finely ground active substance is intimately mixed with theadditives. A suspension concentrate is thus obtained, from whichsuspensions of any desired concentration can be prepared by dilutionwith water.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        Active substance No. 1.29                                                                            5%                                                     Isopropylamine         1%                                                     Octylphenolpolyethylene glycol ether                                                                 3%                                                     (78 mol of EO)                                                                Water                  91%                                                    ______________________________________                                    

Biological examples Example B 1: Herbicidal action before emergence ofthe plants

Plastic pots are filled with expanded vermiculite (density: 0:135 g/cm³,water absorption capacity: 0.565 1/l). After the non-adsorptivevermiculite has been saturated with an aqueous emulsion of the activesubstance in deionized water, which contains the active substances in aconcentration of 70.8 ppm, seeds of the following plants are sown on thesurface: Nasturtium officinalis, Agrostis tenuis, Stellaria media andDigitaria sanguinalis. The experimental containers are then kept in aclimatically controlled chamber at 20° C. under an illumination of about20 klux and a relative atmospheric humidity of 70%. During a germinationphase of 4 to 5 days, the pots are covered with material which istransparent to light in order to increase the local atmospheric humidityand are watered with deionized water. After the 5th day, 0.5% of acommercially available liquid fertilizer (®Greenzit, from Ciba-Geigy) isadded to the water used for watering. 12 days after sowing, theexperiment is evaluated and the action on the experimental plants isevaluated according to the following scale:

1 :plants have not germinated or have completely dried

2--3 : very potent action

4-6 : moderate action

7-8 : weak action

9 : no action (as untreated control).

Pre-emergent action:

Concentration of the active substance emulsion: 70.8 ppm

    ______________________________________                                        Active sub-                                                                           Test plant                                                            stance No.                                                                            Nasturtium Stellaria Agrostis                                                                              Digitaria                                ______________________________________                                        1.01    2          2         2       2                                        1.03    2          2         2       2                                        1.05    2          3         2       3                                        1.11    2          2         2       2                                        1.12    2          3         2       3                                        1.29    2          2         2       2                                        1.57    2          2         2       2                                        1.61    2          3         2       3                                        1.85    2          2         2       2                                        1.89    2          3         2       3                                         1.215  2          2         2       2                                         1.218  2          3         2       3                                        5.01    3          3         3       3                                        7.03    3          6         3       7                                        7.04    1          1         1       1                                        7.06    2          2         2       2                                        7.07    2          2         2       2                                        7.19    2          2         2       2                                        7.58    3          4         3       5                                        7.59    2          2         2       2                                         7.135  2          2         6       7                                        ______________________________________                                    

Example B 2: Inhibition of growth of tropical Leguminosae cover crops

The experimental plants (Centrosema plumieri and Centrosema pubescens)are grown to the fully developed stage and cut back to a height of 60cm. After 7 days, they are sprayed with the active substance as anaqueous emulsion. The experimental plants are kept at 70% relativeatmospheric humidity under 600 lux of artificial light for 14 hours perday at temperatures of 27° C. during the day and 21° C. during thenight. 4 weeks after the application, the experiment is evaluated. Thenew additional growth is estimated and weighed in comparison with thecontrol and the phytotoxicity is evaluated. In this experiment, theplants treated with the active substances of the formula I show a clearreduction in new additional growth (less than 20% of the new additionalgrowth of untreated crop plants), without the experimental plantsthereby being damaged.

Example B 3: Growth regulation in soyabean

Soybeans of the "Hark" variety are sown in plastic containers with asoil-peat-sand mixture in a ratio of 6:3:1 and the containers are placedin a climatically controlled chamber. By optimum choice of temperature,illumination, addition of fertilizer and watering, the plants develop tothe 5-6 trefoil leafe stage after about 5 weeks. At this point in time,the plants are sprayed with an aqueous liquor of an active substance ofthe formula I and are wetted thoroughly. The active substanceconcentration is up to 100 g of active substance/ha. Evaluation iscarried out about 5 weeks after application of the active substance. Incomparison with untreated control plants, the active substances of theformula I according to the invention cause a notable increase in thenumber and weight of pods on the main shoot.

Example B 4: Inhibition of growth in cereals

The cereal varieties Hordeum vulgare (spring barley) and Secale (springrye) are sown in plastic pots with sterilized soil in a greenhouse andare watered as required. About 21 days after sowing, the shoots aresprayed with an aqueous spray liquor of an active substance of theformula I. The amount of active substance is up to 100 g of activesubstance per hectare. The growth of the cereal is evaluated 21 daysafter the application. The treated plants show a reduction in newadditional growth in comparison with the untreated controls (60-90% ofthe control), and in some cases an increase in stem diameter.

Example B 5: Inhibition of growth in grasses

The grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylisglomerate and Cynodon dactylon are sown in plastic dishes with asoil-peat-sand mixture (6:3:1) in a greenhouse and are watered asrequired. The emerged grasses are cut back weekly to a height of 4 cmand about 50 days after sowing and one day after the last cut aresprayed with an aqueous spray liquor of an active substance of theformula I. The amount of active substance, when converted, is up to 100g of active substance per hectare. 21 days after the administration, thegrowth of the grasses is evaluated.

The compounds of the formula I effect a reduction in new additionalgrowth of about 10-30% in comparison with the untreated control.

What is claimed is:
 1. A compound of the formula ##STR41## in which E is═CR⁴ --, R¹ is C₁ -C₃ -halogeno-alkyl, C₁ -C₃ -alkoxy, C₁ -C₃-halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulfinyl, C₁ -C₂-alkoxyethoxy, C₁ -C₃ -alkylsulfonyl, halogen or --NR⁵ R⁶, R³ ishydrogen or C₁ -C₃ -alkyl, R⁴ is hydrogen, C₁ -C₃ -alkyl, C₁ -C₃-halogenoalkyl, C₁ -C₃ alkoxy, cyclopropyl, C₁ -C₃ -halogenoalkoxy, C₁-C₃ -alkylthio, C₂ -C₄ -alkoxyalkyl, C₃ -C₅ -dialkoxymethyl, halogen or--NR⁵ R⁶ and R⁵ and R⁶ independently of one another are hydrogen or C₁-C₃ alkyl, with the proviso that R³ is C₁ -C₃ alkyl if R¹ is methyl, R²is hydrogen and E is the group ═CCl--or ═CH--. 2.3-Amino-5-methoxy-1-methylpyrazin-2-one according to claim 1.